Profiles of Psychedelic Drugs

Nan's Nook : Archives : Botanicals : DMT

Text from a January 1977 journal article by Alexander T. Shulgin

With this issue we are introducing a new column which will present thumbnail sketches of the known psychedelic drugs. Rather than an attempt to review the existing literature on each drug (some would have hundreds of references and some perhaps two), the facts that are known concerning history, human pharmacology and human psychopharmacology will be amalgamated into a "profile." The drugs to be presented will be chosen randomly, rather than with preference given to popularity, unusual potency, or current availability. Botanical mixtures will not be considered as such, but as their known active compnents. As there are upwards of a hundred psychedelic drugs currently known, it is expected that these "profiles" will eventually form an extensive reference atlas of compactly prsented drug information.


1. DMT

Description and properties:

DMT, N,N-diemethyltryptamine, Nigerine, desoxybufotenine, 3-(2-dimethylaminoethyl)-indole is a white, pungent-smelling, crystalline solid with a melting point of 49-50 degrees Celsius, hydrochloride salt hygroscopic, picrate m.p. 171-172 degrees Celsius and methiodide m.p. 215-216 degrees Celsius. It is insoluble in water, but soluble in organic solvents and aqueous acids.


DMT was first synthesized in 1931, and demonstrated to be hallucinogenic in 1956. It has been shown to be present in many plant genera (Acacia, Anandenanthera, Mimosa, Piptadenia, Virola) and is a major component of several hallucinogenic snuffs (cohoba, parica, yopo). It is also present in the intoxicating beverage "ayahuasca" made from Banisteriopsis caapi, and it may have oral effectiveness due to the presence of several naturally occuring inhibitors of catabolic deamination.

Human Biochemistry and Pharmacology:

Both the parent compound tryptamine and the N-methyltransferase system which is capable of converting it to DMT, occur in humans, but there is as yet no evidence that DMT is formed "in vivo". DMT has nonetheless been identified in trace amounts in the blood and urine of both normals and of schizophrenic patients, but its origins and functions are unknown. Following intramuscular administration, maximum blood levels of about 100 ng/ml are observed in 10 minutes, coincident with the maximum changes in electroencephalographic responses. The plasma clearance t-1/2 [half-life] is about 15 minutes. Elevated blood levels of indoleacetic acid (IAA) are seen during the time of peak effects, implying its role as a metabolite. Urine levels of IAA are also elevated and account for about 30% of the administered drug. An increase in 5-hydroxy-IAA excretion suggests the involvement of serotonin in DMT action. Unchanged DMT is not excreted.

Human Psychopharmacology:

DMT is inactive orally at dosages of over 1000mg. With intramuscular injection, there is an abrupt threshold of activity shown with 30mg, and a complete psychedelic experience results from the administration of 50-70mg (75mg subcutaneously, 30mg by inhalation). An unusual feature of the induced intoxication is the speed of onset and short duration. Within 5 minutes of administration there is mydriasis [dilated pupils], tachycardia [rapid heart beat], a measurable increase in blood pressure, and related vegetative disturbances which usually persist througout the drug experience. In 10-15 minutes, the full intoxication is realized, generally characterized by hallucinations with the eyes either open or closed, and extensive movement within the visual field. There is difficulty in the expression of one's thoughts, and in concentration on a given subject. There is usually a mood change to the euphoric with unmotivated laughter, but instances have been reported in which paranoid ideation has promoted anxieties and feelings of forboding into a state of panic. The subject is largely symptom-free at 60 minutes, although some residual effects have been seen in the second hour. With the inhalation route of administration the time scale is contracted, with onset of effects noted in 10 seconds, a short period of full intoxication at 2-3 minute, and a complete freedom from any residual effects within 10 minutes. At higher drug levels, there are increased vegetative symptoms, and these effectively overwhelm the psychedelic experience at dosages of 150mg i.m. Interactions with other drugs are rarely seen; a sensitivity has been observed with pretreatment with methlysergide, but there is no cross-tolerance with LSD. Repeated usage does not appear to lead to either physical or psychological dependency.

Legal Status:

DMT is explicitly named as a Schedule I drug in the Federal Controlled Substances Act; registry number 7435.


Merck Index 11th Ed. Ref RS51.M4 1989

3251. N,N-Dimethyltryptamine.

C12H16N2 - mol wt 188.26; C 76.55%, H 8.57%, N 14.88%

Occurs naturally in plants with hallucinogenic properties.
Isoln from the leaves of Prestonia amazonica (Benth.)
Macbride (Haemadictyon amazonicum Spruce & Benth.),
Apocynaceae: Hockstein, Paradies, J. Am. Chem. Soc. 79,5735(1957).
Synthesis: Szara, Experimentia 12,441(1956)
using the method of Specter, Anthony J. J.Am.Chem.Soc. 76,6209(1954).
Relationship between hallucinogenic activity and electronic configuration:
Snyder, Merril, Proc.Nat.Acad.Sci. USA 54,258(1965).

                         /\   N
                        // \ / \
                       |   ||  ||
                       |   ||__||
                        \\ /     \ 
                         \/       CH2CH2N(CH3)2

Crystals, mp 44.6-46.8. pKa 8.68 (ethanol-water).
Freely sol in dil acetic and dil mineral acids.

Picrate, mp 169.5-170
Methiodide, mp 216-217

Caution: This is a controlled substance (hallucinogen) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.11 (1985).


DMT is Dimethyl Tryptamine = N,N Dimethyl 3-amino-ethyl indole.

It is a powerful hallucinogen, the prototype of this class, and chemically related to psiloc(yb)in and more distantly to LSD.

Dose: around 60 mg.

Method of ingestion: usually smoked (inactive orally at reasonable doses.)
Can be combined with monoamine oxidase inhibitors (MAOI) to make it orally active and increase the duration. Could be snuffed or or injected.

Duration of action: 2-5 minutes of peak, around half an hour of cruise.

Side effects: Stimulation and tactile hallucination during trip. No perceivable after-effects. No known long term side effects. May be some link with schizophrenia, since it has been detected in vivo.

Status: illegal in USA, Australia, most places.

History: is a component of some snuffs used by South American natives. also used in combination with MAOIs (harmaline etc.).

Availability: Very rarely available from dealers; rarely synthesised. Available from a range of natural sources.

Psychological effects: A very intense but brief trip, not really euphoric. Can be frightening because of the sudden onset. Not really a party drug, rather an interesting experience. More intense than LSD, but hallucinations and perceptual changes are of a somewhat different nature.

(these are only my opinions and recollections)


There are three issues here which are a little confused:

  1. Strength in the sense of effective dose,
  2. Strength in terms of subjective intensity,
  3. Being a superior hallucinogen in some subjective sense.

Comparing DMT and LSD, the first is easy.
The effective dose of LSD is around 100 ug, of DMT is around 60 mg, so in this sense, LSD is a much stronger hallucinogen.

In terms of intensity, they are difficult to compare. Part of the intensity of DMT stems from the fact that the onset is virtually instantaneous; one is taken from feeling normal to the peak of the trip in the space of a few seconds, and this can be totally disorienting and frightening. DMT does not have the euphoria of LSD, in fact it can be quite uncomfortable. Also, the smoking of DMT is quite unpleasant compared with eating some small object. The types of hallucinations experienced within the peak of the DMT trip differ markedly from those in the peak of the LSD trip. This difference is very hard to describe, although one might contrast the dripping flowing colourful experience of LSD with the DMT visuals in which everything becomes super sharp to the point of being ripped into fragments, like placing a photo in a blender. There is some colour enhancement, but it is more like lightning-bolts of colour rather than flowing ripples of colour, and colours may be actually entirely changed and several multiple images seen at once. The 20-30 minute come-down of DMT is similar in experience and intensity to a small dose of LSD, however one is likely to be too shattered by the initial peak to worry about this much. The account Bob posted is highly subjective and metaphorical (as is this one, I suppose) and I doubt that many people would experience DMT in the way described there. However, extending the duration of DMT by the use of monoamineoxidase inhibitors (Ayahuasca,Yage,etc.) is supposed to be a very intense experience and could give one time to become more involved in it. It is possible to lose all contact with the senses and the world briefly while on DMT, as it is, e.g. from a combination of nitrous oxide and LSD. Also, psiloc(yb)in seems to have some similarity to DMT whilst retaining similarity to LSD, in that during the psilocin experience one can be transported into a different reality, although one which is still definitely based sensually on this one, and not be able to remember or understand everday reality. Other hallucinogenic experiences, e.g. the delerium caused by anti-cholinergics, might be still more intense than DMT in terms of being completely removed from traditional reality, but I don't think anyone would recommend experimenting with these dangerous substances.

In terms of which is the superior hallucinogen, it depends on your taste. DMT is very interesting and extremely intense, but not necessarily pleasant. LSD has more potential for pure recreation. Most people would probably prefer LSD as a recreational hallucinogen, and it would be ill-advised for someone who was not very familiar with coping with the intensity of LSD to be thrust into the intensity of DMT. On the other hand, if you don't like DMT, you only have to hang on for a few minutes, whereas if you don't like LSD you have to hang on for several hours.

This is, of course, apart from the dosage, all subjective. (L`HOMBRE INVISIBLE) writes:

>Many plants contains psychedelic tryptamines :

> Piptadenia Peregrina
> Phalaris Grundinacea
> Mimosa hostillis
> Desmanthes illioiensis
> Arundo Donax
> etc.

>The DMT/5-methoxy-DMT ... is often located in the roots of the plant

Depends on the species - some contain it in the leaves or the bark.

>My question is :
>Is it possible to smoke the plant-material directly or do you have to
>it first ?.

I don't know as much about 5-Me-O DMT as DMT. THere is an important difference, which is the dose. The former is effective at about 5mg-10mg from memory, the latter at 30-60mg. Thus, it is possible to obtain sufficient 5-Me-O DMT from smoking some impure unrefined sources (such as the poison of Bufo alvarius).. Considering DMT as opposed to 5-Me-O DMT (which is IMHO by far the more desirable material), and recalling that most people find the peak of a DMT trip only to last a very few minutes after smoking (i.e. you have to smoke it all at once, within a few tokes, to obtain the peak) you can easily calculate the necessary purity. Let us say, that one is capable of smoking 100mg of material in a few seconds. THis means that a DMT containing mixture should be at least 30% pure to get sufficient effect, and a 5-Me-O DMT mixture should be at least 5% pure. In actual fact, it is not quite as bad as this, because if you are using a free-base pipe, you can get away with lower purities because the DMT is quite volatile, so initially, the smoking process will concentrate the DMT.

Comparing this to plant matter, which might be e.g. 0.3% DMT, and you see at once, that you would need to smoke about 10 g in a few seconds which is unrealistic. Hence, chemical purification is necessary.

The alternative is to take the plant source orally in combination with the hallucinogenic monoamineoxidase inhibitor harmaline (and related alkaloids). These are most readily obtained from Peganum harmala (or Banisteriopsis caapi) and serve to activate and potentiate tryptamines, increasing intensity and duration and giving oral activity to DMT.

> What are the effects (Like the pure stuff (DMT)) ?

A small amount gives a wierd feeling in the body and some perceptual change. A larger amount gives strong body feelings and heavy visual effects , somewhat similar to LSD, but much more based around geometry, and changes of shape perception. A very large dose is totally awesome, and people's responses differ, from catatonia, to screaming, to total ecstasy. Some people describe it as a religious experience. Many people find they completely leave our universe for the duration, which is generally up to 5 minutes, with residual effects up to half an hour.

>Which plant(s) are best suited ? (Highest in DMT)

There are various possibilities. Since chemical purification is generally necessary, the plant content is not vitally important. Most important is supply - the best species is one which grows locally, and in the US, the best source is probably Desmanthus illinoensis.

If you wish to receive instructions on how to chemically purify DMT from a plant source, and more information about the effects of DMT, mail me at:

but do not hassle the owner of this account by replying to this address.


{In article <[email protected].com>, [email protected] (Curious Furious) writes:
> Hi knowledgeable folks,
> I have a few questions from a FOAF:
> 1) When smoking DMT what is the LD50 ? Can it cause a heart attack?
Certainly much higher than the amount beyond which one would have no concept of what a pipe, DMT, oneself, etc. is. Also much higher than the amount one could get into ones body by smoking before it was metabolised. I imagine that even if one hooked oneself to a machine which continously fed oxygen, nitrogen, and DMT vapour it would still be hard to _physically_ overdose. As for heart attack, I have no idea. I can imagine being scared to death (literally).

> 2) Has anyone tried doing DMT while on MDMA ? Any complications ?

No idea. However, one of the most striking things about DMT is its brutalness - the rush from completely baseline to another universe in about five seconds. Starting off baseline does little to alter the peak (which tends to override anything) but alters the severity of the onset.

> 3) Has anyone tried doing DMT while on 'rooms? Any complications ?

Yup - similar to above, except moreso. It takes a large dose for the effects of the DMT to become visible over the effects of the trip (likewise for LSD). Also, it is harder to trip on DMT post psilocybin or LSD, since there is some cross tolerence.

Some combinations with DMT are worthwhile. A couple of beers beforehand bluntens and deadens a little which can be very helpful. A good amount of heads will add to the visual impact, and a good amount of hash will ad to the wierdness and otherness. N2O & DMT is interesting, but the combination is generally intense enough to cause amnesia, and lack of any kind of regular consciousness for the period of intoxication.

> 4) In the book _Archaic Revival_, Terence McKenna mentions some studies
> that found that DMT is produced heavily while in the deepest stages
> of sleep. Anybody have a reference for that?

Interesting concept. Like much of McKenna's work, I expect that the science to back him up is scanty, non-existant, or occasionally wrong. Makes for a good story, though.

> 5) Since DMT is a naturally occurring substance in the human body,
> if a machine was created which could extract DMT from your own
> blood, would that machine be considered illegal?

My limited understanding of US law suggests that if humans contain DMT then their entire weight can be counted as DMT (since the carrier weight can be included) Such a theoretical machine as you suggest would be covered by paraphernalia laws?

> 6) Can any MAOI be used to render DMT active orally?

Lamont is the expert on this, and he says yes. I am not convinced, and I don't think there is any proper research published on the subject. Even in the case of the traditional harmaline/DMT interaction, the scientific data is minimal, and it is surmise only that the DMT is orally activated by the MAOI effect of the harmaline and not by some other effect. I hope someone else will fill in the missing details.

> thank you for your time.

my pleasure.


With respect to orally activating DMT with an MAOI, Dennis McKenna has this to say in his '84 review article in J. Psych. Drugs 16(4):


"The potentiation of the behavioral and pharmacological effects of tryptamine derivatives by MAOIs has been investigated, although the specific question of the oral potentiation of DMT and other parenterally- active derivates has apparently not been investigated. The effects of DMT in human volunteers was assessed before and 3 days after treatment with the MAOI iproniazid (Sai-Halasz 1963). Patients receiving DMT at a reduced dose following the iproniazid treatment experienced none of the visual illusions or disturbances of time and space perception that typify the symptoms of the drug. They reported only a feeling of "strangeness." Patients receiving a dose equivalent to that prior to iproniazid had a two-phase response. The first stage was similar to the usual DMT effects, but less pronounced: illusions and hallucinations were present but less colorful and only manifested themselves with the eyes closed. The second phase was characterized by a persistent feeling of "strangeness" to which the patients often reacted negatively or indifferently. Based on these trials, Sai-Halasz (1963) speculated that the reduced effects may have been due to the higher 5-HT concentration in the brain due to MAO inhibition, thus mitigating the 5-HT blocking effects of DMT. This speculation was also supported by the observation that prior administration of 1-methyl-d-lysergic acid butanolamide, a powerful serotonin antagonist, greatly exacerbated the psychotomimetic effects of DMT (Sai-Halasz 1962)."

So, it would appear that the answer to question 6 hasn't been established. However, some studies (mentioned above) seem to have been done demonstrating an interaction between MAOIs and DMT.

J handled most of those questions better than I could, so I don't have much else to add. I doubt there have been any deaths attributable to DMT use. Also, I don't recall endogenous DMT in humans and Dennis doesn't mention it in his review article so it is either recent (post 1984) knowledge or it is a misprint by the poster or publisher and should refer to a related tryptamine. Or maybe it's another revalation from the self-constructing machine elves.

[email protected]


Newsgroups: alt.drugs
From: J
Subject: Re: DMT Ingestion Methods
Date: Thu, 1 Jul 1993 14:53:35 GMT

DMT is a powerful hallucinogen. No one should take it for granted or use it lightly. It is also illegal, although natural sources are uncontrolled.

In article <[email protected]> Nathan.Bowen writes:
> Lately, there has been an increasing interest among alt.drugs
>posters concerning DMT in its many forms. I'm finding the many accounts
>of experiences quite intriguing, but I am still pretty thoroughly in the
>dark concerning methods of usage. I believe I understand to a
>reasonable extent the various methods themselves, but I cannot find
>sufficient information on the benefits or drawbacks of them. I seek
>both scientific evidence and subjective reports of the desirability of
>given methods from people who are in a position to know.
> In my understanding, eating/drinking is probably the least desirable
>method, in that it requires a monoamine oxidase inhibitor to be active

Each method of ingestion has its own advantages and disadvantages.

Oral DMT/harmaline is potentially the best method of ingestion in terms of having a truely profound experience of useful duration. Coming on to the experience a little more slowly gives the user some time to adjust and to cope with and explore the altered state. Oral DMT is probably the only viable route for most alt.drugs readers, who can obtain the plants but who don't have the necessary experience and equipment to sufficiently purify DMT for smoking, and who do not have access to synthetic DMT. Unfortunately, the liquors produced by boiling up plant DMT sources may well make the user puke.

>Although an account of a very successful ayahuasca experience
>was recently posted that confirmed the possibility of desirable effects
>resulting from oral consumption, the prolonging effect of the
>preparation involved seems to undermine the highly-acclaimed temporariness
>of the DMT experience (hence the Businessman's Trip).
Well, the temporariness makes the intensity bareable when the material is smoked. The oral experience is gentler, but just as profound, if not moreso. Smoked DMT is so brutal, and the effect can be so profound, that after much experience, all I could say was that I couldn't say anything adequate about it, and so I gave up on it.

> The most common form of ingestion, at least among the accounts on
>the 'net, is smoking. There are inherent disadvantages to inhaling the
>gases given off by burning matter, but I don't see any way around it,
>and it seems that smoking is also the most accepted method for a
>pleasurable experience.

Don't make the mistake of calling DMT pleasurable - that may or may not be one of its side-effects :). In fact, apart from the physical, smoked DMT is more likely to be dysphoric than oral DMT. A single user may have one DMT trip which is totally orgasmic, and then another which is totally horrific, and then another that is neither. Smoking the chemical is particularly unpleasant to the mouth, throat, and lungs, and some people find it an impossible task.

> I don't see how, logically, a water bong or
>some such device could be implemented here, but I'm definitely willing
>(and eager) to be proven wrong.
Hot DMT vapours are somewhat soluble in water; if you are smoking the chemical, then mostly what you are getting is its vapour, and there is little you can do to improve the quality.

> The other methods that have been mentioned are snuffs (a la the
>native South American rituals)

The South American snuffs contained various tryptamines. It is well nigh impossible to get a sufficient dose of DMT from a snuffed plant source - the concentrations just aren't high enough. Likewise smoking a plant. The major active in the snuffs was probably 5-MeO-DMT.

> and injection (for which I can find no

Lots of experiments in the 60's. If you have something pure enough to inject, you might as well smoke it and save yourself the hassle. Likewise, there is probably little advantage to snorting the pure chemical over smoking it.

Newsgroups: alt.drugs
From: [email protected] (Pierre St. Hilaire)
Subject: Re: DMT Ingestion Methods
Message-ID: <[email protected]>
Date: Thu, 1 Jul 1993 14:50:39 GMT

> The other methods that have been mentioned are snuffs (a la the
>native South American rituals) and injection (for which I can find no
>references). The snuffs have been reputed as bringing on rapid and
>powerful effects, and that seems to correspond with my knowledge of
>snuffed/injected drugs. I do not, unfortunately, have a sufficient
>amount of information on the safety of these methods. I do understand
>the inherent dangers of sending the material directly to your
>bloodstream, in that any impurities will follow just as easily. Other
>than that, I am fairly in the dark. This is where the bulk of my
>request lies. Are these methods as efficient and desirable as they seem
>at the outset? And, even if they aren't, how do they rank with oral use
>or smoking? Opinions are as welcome as facts, and any reply will be
>greatly appreciated. If I get a large enough response, I'll try to
>compile a FAQ or short informational file of some sort.

My experiences and those of others point to the fact that the subjective effects of tryptamines vary markedly with the route of absorbtion. While smoking often results in overwhelming experiences it is possible to have more psylocibin like effects by snorting or eating small amounts in conjunction with P harmala seeds. It seems also that 5-MeO-DMT and DMT, whose effects differ considerably when smoked, seem to "converge" in subjective effects when taken orally. I wonder if other knowledgeable people on the net could substanciate that last claim.

Of all the psychedelics, short acting tryptamines seem to have the most non linear dose-responses curve. Taking twice a barely active dose will often result in an intense experience! That is the reason why you should be very careful when taking them orally.

I recently found a very interesting and potentially safer way to use 5-MeO-DMT. The key is to dissolve it in distilled water and put the solution in one of those nose spray bottles in such a way that each inhalation will dispense about 3-4 mg (Don't screw up there!). When taken as a nose spray the effects come on more slowly than smoked (about 1 min. instead of a few sec.) and the effect is more spread out in time. The nice thing is that it is possible to very accurately control the dose, which makes the trip a lot more manageable. Taken in that manner, the effect can be fairly similar to psilocybin, with the advantage that it is possible to come down within half an hour. I guess this method could be used with DMT, but you would probably have to convert the base into a salt (for higher solubility) since you need a 10x higher concentration of DMT in the solution.

Pierre St Hilaire
MIT Media Lab


From: [email protected] (John Eichenseer)
Newsgroups: alt.drugs
Subject: Re: DMT extraction
Date: 11 May 1994 13:19:35 -0500
Message-ID: <[email protected]>

>I am trying to extract DMT from Desmanthus illinoensis.

Ah, good luck, and do post your results...

> So, what do you think? Will this method work? Is there any
>better way that is easier (this is pretty easy) or more efficient?

In his book Pharmacotheon, Jonathan Ott mentions experiments in which he extracted the alkaloids via boiling water. In fact, I think he may have just strained hot water through the finely ground material, like making coffee. He did this in order to mix it with an MAOI (harmala seeds) for oral ingestion. I believe he goes into much more detail in his latest book, Ayahuasca Analogs.

Can anybody comment on the viability of this technique? It does seem even easier than the acid-base extracion, although of course it would not yield the smokable freebase.

Just curious,

[email protected] (Robert R Pascazio) writes:

> Has anybody heard stories about Arundo donax (aka "Giant Reed") ? It
> is rummored to contain DMT and other exciting Alkaloids.

Yes. It contains some DMT, but not very much. Someone told me the other day that a friend of theirs that is investigating this (solicited samples from interested parties, and used thin layer chromatography to assay the root stocks, from what I was told) says there's "little or no DMT" in Arundo donax rhizomes.

The paper that first found DMT and a few other indole alkaloids in Arundo donax (Ghosal) working in India (River Reed is used in Ayurvedic medicine) also found only trace amounts. You'd have to extract several kilograms to get a psychoactive dose of DMT. There are also several cardioactive glycosides and other substances that would produce annoying side effects if a crude extract were consumed - the effect of Arundo donax extract on heart muscle (another paper by Ghosal et. al.) gave me the impression that crude Arundo extracts are potentially dangerous. You'd have to resort to solvent extraction followed by column chromatography to extract pure DMT from the roots - a process probably requiring several liters of solvent just to produce one dose of DMT.

I'll shell to DOS here and see if I can find my notes about Arundo donax...

ok... here's a good starting point if you want to look into this:
DMT in Arundo Donax / Giant River Reed
"Tryptamines and Related Compounds in Plants"
Phytochemistry, 1977, Vol.16 pp 171-175

ABSTRACT: The occurrence of the tryptamines and related compounds in fungi and higher plants is listed on a taxonomic basis. Several of these amines have considerable physiological activity in higher animals.


    Arundo donax L. (Leaf,Flower,Rhizome) [27-30]

  • Methoxy-N-methyl-Tryptamine
  • DMT
  • DMT-Methohydroxide
  • Bufotenine
  • DMT-N-oxide
  • Bufotenidine
  • Dehydrobufotenine
  • Gramine
  • Gramine-N-oxide
  • Gramine methohydroxide

[27] OREKHOV AP, NORKINA SS (1937) Zhur.Obsch.Chem. 7,673
[28] GHOSAL S, BANERJEE PK, BANERJEE SK (1970) Phytochemistry 9,429
[29] GHOSAL S, CHAUDHURI RK, DUTTA SK (1971) Phytochemistry 10,2857

Tryptamines in the Graminacea:

Arundo donax - Giant River Reed
Phalaris arundinacea

_A Handbook of Alkaloids and Alkaloid Containing Plants_
Wiley Interscience, Raffauf QK898.A4 R34 (1970)


N,N-DMT GRAM-028A refs:1946, 573
Bufotenine GRAM-030A refs:1945
Gramine GRAM-016A

573 Aus J. Chem 17:1301 (1964) [Phalaris]
416 Aus J. Chem 19:893 (1966) [Phalaris]

1946 Dutta,SK;Ghosal,S _Chem.Ind._ (1967) p2046
1945 Moore,RM; Williams,JD; Chia,J _Chem.Abst._ 68:75704v (1968)

574 Ghosal,S; Mukhergee,BB _Chem.Ind._ (1965), 793
575 Morinato,H; Matsumoto,N _Am.Chem._ 692 p194 (1966)

464 Legler,G; Tschesche,R _Naturwiss_ 94 (1963)




  • _Tryptamine and related compounds in plants._ SMITH, TA. "Phytochemistry." vol.16 pp.171-175. (1977) QK861.P45
  • _The Occurrence of Indolealkylamine Alkaloids in Phalaris tuberosa L. and P. arundinacea L._ , Culvenor,Dal Bon & Smith "Australian Journal of Chemistry" 1964, Vol.17 pp.1301-4
  • _Heterocyclic Compounds, Indoles, Part 2_ Houlihan, Wiley Interscience, pg264
  • _Indole alkaloids in plant hallucinogens_ Schultes, Richard Evans "Journal of Psychedelic Drugs" Jan-Mar 1976 p17
  • _Plants of the Gods_ Schultes & Hofmann
  • _Narcotic Plants_ William Emboden
  • _Tryptamine and Related Compounds in Plants_ Terence A. Smith. "Phytochemistry" Vol. 16 pp. 171-175
  • _Alkaloid Bearing Plants and Their Alkaloids_ US Dept. Agriculture Technical Bulletin No. 1234 (1961) Willaman & Schubert
  • Erspamer _???? Drug Res._ 1961,3,151


From: [email protected] (Rocky Frisco)
Newsgroups: alt.drugs
Subject: Ayahuasca....more info ne
Message-ID: <[email protected]>
Date: 29 Jan 94 02:37:00 GMT

AA> Thank you everyone who e-mailed me information on Yaje. If anyone
AA> else has more info, I still need it. Please post or e-mail me. I
AA> would especially like to hear from people who have experimented with
AA> Yaje. Did you smoke it or did you drink it? Thanks, Ayleen
AA> [email protected]

I think it's usually spelled "Yage" pronounced Yah-hey.

See the books "Wizard of the Amazon" and "Rio Tigre" by the late Doctor Bruce Lamb of Santa Fe NM. (Bruce died during the Christmas Holiday season of 1992). These are the best resources on the subject and are written by a fine scientist who tried Ayahuasca and found it to be of great value.

-Rock [email protected]
* RM 1.2 * Eval Day 7 * RoboMail -- The nag nag nag


From: Richard Hodges
Newsgroups: alt.drugs
Subject: Ayahuasca
Date: 10 Aug 1994 00:07:04 GMT
Message-ID: <[email protected]>

I just returned from a trip to Brazil, where I became aware of several contemporary movements which practice some form of ritual centered around taking Ayahuasca. The group I contacted is called "Santo Daime" which means, in Portugese, "Holy Give Me." What they want to be "given" is defined as "Love, Truth, and Justice." A noble prayer, IMHO!
Anyway, it was claimed that Santo Daime has a large and growing following in almost all countries of the world, except for the USA, where it is prohibited.
My question is, does anyone have any knowledge of the current status, legal and operational, of Santo Daime and other Ayahuasca rituals in the US?

From: [email protected] (Diablo)
Newsgroups: alt.psychoactives
Subject: Re: a DMT trip
Date: 22 Apr 1994 06:45:27 GMT

[quoted text deleted -cak]

Here is an interesting description of DMT from the book "Cyberia" by Douglas Rushkoff:

"For those still intent on smashing the ego into oblivion and discovering the very edge of what it means to be sentient, DMT (dimethyltryptamine and its cousin 5-hydroxytryptamine) is the only user described it saying "It's like taking every LSD experience you've ever had and putting them on the head of a pin."...It's effect is immediate--definitely within a minute, usually within seconds--and all-encompassing. It cannot even be described in terms of magnitude, but makes more sense when thought of as a true, hyperdimensional shift."

He goes on to talk about someone else's description of DMT, using much shaman babble that I'm not interested in. However, later, he talks about this place in the hills behind Oakland where a bunch of college age students live in a commune and regularly do DMT while being observed by this 30 year old doctoral thesis candidate. He is writing his thesis on shared states of consciousness. Anyhow, when the writer was there, Dan (the thesis dude) had just gotten hold of a new, synthetic and more powerful version of DMT made by a chemist whom you meet earlier in the book (this is all true btw). The new stuff is called "5 Mao DMT" and apparently is close to the strength it takes to literally fry your brain. This stuff sounds incredibly intense to me. Some guy named Armand (who, incidentally, had been taking acid every day for the past week in order to prepare for this little ritual) takes his hits and spaces out for ten minutes, comes back, and details that he has been gone for three days. He says he met an entire race of forest creatures and they needed his help. He even made love to one of them.

Anyhow, another guy, who has had a bad day and is looking for an awesome trip does it and has a very BAD trip. He freaks out and thinks that Dan is his creator because he gave him the DMT and that he (the fucked up guy) only exists when Dan gives him DMT.

Well, I'd be tempted to try this stuff even though I have relatively limited experience with shrooms and acid and none at all with peyote but I'm not sure it's such a good idea. I'm always looking for an all-encompassing experience but DMT sounds like it's over the edge. The fact that it only lasts 10 minutes or so is really no comfort since I generally have zero sense of time on hallucinogens; I could be tripping for 10 hours or ten minutes.. wouldn't matter much to me at the time, only the "now" exists when I'm tripping.

Sorry this was so long.



I mentioned in passing the other night that I was interested in various things, one of which was the use of Ayahuasca, a brew made by sorcerers living along the Amazon River in South America.

I'd like to explain some of the thing's I've learned about this and see if you have any comments about or interest in them.

Ayahuasca is made by brewing the stems of a vine called Banisteriopsis with parts of at least one other variety of plant. The spirit of the banisteriopsis plant is supposed to act as a guide for the spirits of the additive plants and potentiate thier effects. Different additive plants are used for different purposes: soul travel, telepathy, healing, communicating with spirits, visions, divination, or learning spirit songs (something in which I am particularly interested - I occasionally hear music in dreams and write it down or play it after I wake up), etc. Some of the main additive plants are Psychotria, Justicia, and Tetrapteris. Strangely enough, all three of these plants contain DMT. The guide plant itself contains a drug called Harmaline.

Normally DMT is not active when taken orally - it has to be smoked (and there are several other snuffs and smoking mixtures in jungle sorcery that do contain only DMT). But it's been found that harmaline prevents the breakdown of DMT by the digestive system and allows it to enter the bloodstream when one drinks Ayahuasca. Harmaline also extends DMT's visionary effects for up to 6 hours. So it turns out that DMT, which I had always considered to be an exotic laboratory drug, has actually been used by sorcerers in the Amazon for thousands of years.

In Europe and the Middle East, there are also plants which contain harmaline and DMT: Syrian Rue and the Giant River Reed. Though there's no clear evidence that either plant was ever used for sorcery.

Now Syrian Rue itself is quite interesting...
Seeds of Syrian Rue are made into a red dye which is used by middle eastern carpet weavers for coloring Persian Rugs. It has been said that the hallucinogenic properties of a brew made from these seeds may be responsible for the legends about flying carpets. Perhaps the red dye doubled as a beverage, and the patterns on the carpets were actually maps into a magical world. These seeds also contain Harmaline.

The Giant River Reed is significant as well; it's considered the best reed to use for musical instruments, and is the reed traditionally used in the construction of Pan Pipes. And it's roots contain DMT.

Another funny thing is that toad skins (often listed as an ingredient in European witches brews) contain a hallucinogen called bufotenine. I've heard stories of people in Australia actually smoking the skins of roasted Cane Toads as a psychedelic. However, I'm a bit of a vegetarian, so this has limited appeal.

Anyway, I'll enjoy any response to this that you'd care to make.

[E-Mail ... 22-JUN-89]




[Excerpt from a pharmacology textbook published in 1988]

Chemical structure and source:

This is the prototype member of the tryptamine subclass of indole derivatives. The structural formula is:

                         /\       (CH2)2-N(CH3)2
                        // \ ____/
                       |   ||   ||
                       |   ||   ||
                        \\ /\   / 
                         \/  \N/


The drug is a constituent of many of the same South American snuffs and drinks that contain other psychedelic indole deriviatives, it is often found in the same plants as 5-MeO-DMT, and Indians add a substance containing it to drinks containing harmala alkaloids. DMT is the major constituent of the bark of Virola calophylla, mentioned above; it is also found in the seeds of Anadenanthera peregina; in the seeds of the vine Mimosa hostilis, used in easter Brazil to make a drink called "ajuca" or "jurema"; in the leaves of Banisteriopsis rusbyana, which are added to the harmaline drinks derived from other plants of the Banisteriopsis genus to make "oco-yage"; and in the leaves of Psychotria viridis, also added to the Banisteriopsis drinks. Like 5-MeO-DMT, DMT must be combined with monoamine oxydase inhibitors to become active orally.


First strong effects are felt at about 50mg, whether it is smoked or injected. Tolerance develops only after extremely frequent use - injections every two hours for three weeks in rats; at that dose frequency, but not otherwise, there is also a cross-tolerance between DMT and LSD (Rosenberg et. al. 1964; Kovacic and Domino, 1976).

Physiological effects:

Resembles LSD, but sympathomimetic symptoms like dilated pupils, heightened blood pressure, and increased pulse rate are more common and more intense.

Psychological Effects:

Like LSD but often more intense. Since it is not taken by mouth, the effects come on suddenly and can be overwhelming. The term "mind blowing" might have been invented for this drug. The experience was described by Alan Watts as like "being fired out of the nozzle of an atomic cannon" (Leary 1968a p.215). Thoughts and visions crowd in at great speed; a sense of leaving or transcending time and a feeling that objects have lost all form and dissolved into a play of vibrations are characteristic. The effect can be like instant transportation to another universe for a timeless sojourn.

Duration of action:

When DMT is smoked or injected, effects begin in seconds, reach a peak in five to twenty minutes and end after a half hour or so. This has earned it the name "businessman's trip." The brevity of the experience make its intensity bearable, and, for some, desirable.

At least two synthetic drugs in which the methyl group of DMT is replaced by a higher radical are psychedelic:


              /\       (CH2)2-N(C2H5)2     /\      (CH2)2-N(CH2CH2CH2)2
             // \ ____/                   // \ ____/
            |   ||   ||                  |   ||   ||
            |   ||   ||                  |   ||   ||
             \\ /\   /                    \\ /\   / 
              \/  \N/                      \/  \N/
                   H                            H

        N,N-diethyltryptamine          N,N-dipropyltryptamine

The drug DET is active at the same dose as DMT and the effects last slightly longer, about one and a half to two hours. DPT is longer-acting still and has fewer autonomic side effects. In therapeutic experiments its action continues for one and a half to two hours at the lowest effective dose, 15 to 30mg, and for four to six hours at doses in the range of 60 to 150mg. Both DET and DPT are milder than DMT. The drug 6-FDET (6-fluorodiethyltryptamine) resembles DET in its effects. All these drugs, like DMT, are inactive orally and must be smoked or injected. Dibutyltryptamine (DBT) and higher substitutions are inert, but other synthetic drugs related to DMT may be psychoactive.


Message-ID: <[email protected]>
Newsgroups: alt.drugs
From: [email protected]
Date: Thu, 9 Jun 1994 10:35:42 UTC
Subject: How to get smokable DMT from Phalaris arundinacea.

I was at our local hip bookstore this afternoon (picking up a $2 paperback of "The Sacred Mushroom and the Cross" out of curiosity) when I spotted the owner deboxing a bunch of interesting-looking paperbacks. Among them was something called "Psychedelic Shamanism" by Jim DeKorne (Loompanics Unlimited). I grabbed a copy, intrigued by a back-cover legend which promised "Smokable DMT from Plants (A new discovery that will revolutionize psychedelia!)"

Since this has been a big topic hereabouts, I'll summarize his findings:

The headline here is that he uses Phalaris arundinacea, a grass which resembles most folks' front lawn. It's very easy to grow (I grew some from seed once... it took almost no effort and very little time) and you don't have to kill the plant to harvest - just trim the stalks and leaves.

He's taken a Phalaris extract in an ayahuasca-type potion on several occasions, and has given this mix to others, and if there are any other nasty chemicals in Phalaris, they haven't caused any immediately noticable bad effects.

He says he discovered that you could make a smokable extract by accident, after leaving an extract intended for ayahuesque use out where the alcohol evaporated, leaving "a gummy tar" which he "on a sudden whim" decided to smoke. "I took one inhalation of this essence and found my mind immediately blasted into a cerebral hurricane of rapidly pulsing white light. Fortunately, I already knew what a DMT flash is like, so I was not totally taken by surprise."

    His idea of extraction is this:


  1. Pulverize the grass clippings
  2. Add water, "enough... to make a pourable soup"
  3. Acidify to pH 5 or so
  4. (Optional) Simmer the acidified soup in a slow cooker overnight, not allowing the liquid to evaporate. ("It may take two or three such operations to get all of the alkaloids into solution")
  5. Strain the plant matter through cheesecloth, then through a paper coffee filter
  6. Add 10-15% of the mass of the solution in a "defatting solvent" such as methylene chloride, ether, chloroform, or naptha.
  7. Shake vigorously
  8. The crap will go into the solvent, leaving the good stuff in the water.
  9. Separate the water from the solvent.
  10. Add a base to the aqueous solution in small increments until the pH gets to about 9 or 10. This converts the alkaloids into their free base.
  11. Extract with 10% of the mass of the solution of an organic solvent four times, at one 24-hour and then three weekly intervals. The solvent layer will take on a darker tint, usually yellowish or reddish-brown. It will take almost a month to extract all of the alkaloids, and the solution should be shaken at least twice a day between extractions.
  12. Evaporate the solvent off from the combined extract fractions. You now have the alkaloids.

He was smoking 50mg of this goo at a shot.

As a footnote, he tried similar stuff with Arundo donax and got some really nasty reactions from whatever other crud was in the plant. I'm gonna cross this one off of my list.


From: [email protected] (John Spinnato)
Newsgroups: alt.drugs
Subject: DMT extraction from Phalaris
Message-ID: <[email protected]>
Date: 5 Oct 94 20:25:00 GMT

If anyone has a recipe for GHB, Gamma-Hydroxy-Butyric Acid, or Sodium Gamma-Hydroxy-Butyrate, please e-mail me, or leave a message. I am willing to pay for a relatively easy process which doesn't involve exotic chemicals or sophisticated equipment.

DMT extraction from Phalaris grass:
The latest info from The Entheogen Review is that one can avoid chemical extraction altogether, and use a wheatgrass juicer. Jim DeKorne is the editor of this excellent newsletter, as well as the author of Psychedelic Shamanism. Mr. DeKorne warns readers to exercise caution when using extracts from Phalaris until more is known about it.

According to a Soma Graphics report, the following info is taken from a letter by Jim DeKorne:

"The latest scoop is that you don't even have to use chemical extractions anymore - run several handfuls of grass through a wheatgrass juicer (sold in most health food stores) and you'll wind up with a glass or so of incredibly potent liquid. One teaspoon (with MAO inhibition, of course), is a standard dose with strong grass. Only two teaspoons proved very challenging to one of my correspondents - an OD! The juice can be dried and smoked in a bong - two tokes will usually do it."

For more information, refer to the following sources:


The Entheogen Review
P.O. Box 778
El Rito, NM. 87530
subscriptions are $20.00 for one year.

Soma Graphics
P.O. Box 19820
Sacramento, CA. 95617-3481

Acme juice extractors
70-18 71st Avenue
Glendale, NY 11385