The Psychedelics and Related Compounds

By: Adam Pringle

I. Tryptamines
Precursors:
Tryptophan
5-HTP

-carboxyltryptamine
5-hydroxytryptophan

Neurotransmitters and Hormones:

Serotonin
5-hydroxytryptamine
Melatonin
5-methoxy-N-acetyltryptamine
Empathogens:
ET
MT

-ethyltryptamine (Monase)
-methyltryptamine

Psychedelics:
DMT
5-MeO-DMT
5-HO-DMT
4-HO-DMT
Psilocybin
DET
DPT
DiPT

N,N-dimethyltryptamine (Spice, Ayahuasca1)

5-methoxy-N,N-dimethyltryptamine
5-hydroxy-N,N-dimethyltryptamine (Bufotenin)
4-hydroxy-N,N-dimethyltryptamine (Psilocin)
4-phosphoryloxy-N,N-dimethyltryptamine (Shrooms2)
N,N-diethyltryptamine
N,N-dipropyltryptamine
N,N-diisopropyltryptamine

II. Lysergamides: Ergine (LSA), Ergotamine (Cafergot3), LSM, LSD (Delysid), AL-LAD, ALD-52
III. Phenethylamines
Neurotransmitters and Hormones:4
Dopamine
3,4-dihydroxyphenethylamine
Norepinephrine
,3,4-trihydroxyphenethylamine (Noradrenaline)
Epinephrine
,3,4-trihydroxy-N-methylphenethylamine (Adrenaline)

The term ayahuasca can refer to a) a preparation of Caapi vine alone, b) a preparation of a DMT containing plant and Caapi vine together,
or c) any preparation containing any source of DMT and any source of RIMAs (such as Syrian rue extract).
2
Psilocybin the considered the main active ingredient in psychedelic mushrooms. In the body, psilocybin is broken down (by
dephosphorylation) into 4-HO-DMT, a.k.a. psilocin.
3
Cafergot is combination of ergotamine and caffeine.
4
Precursors: L-4-hydroxyphenylalanine (L-tyrosine), L-3,4-dihydroxyphenylalanine (L-DOPA). Note that the tryptamine precursors are
tryptamines, while the phenethylamine precursors are not themselves phenethylamines.

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III. Phenethylamines (continued):

Stimulants:
Methylphenidate
Phenylephrine
Amphetamine
Methamphetamine
Ephedrine
Cathine
Cathinone
Bupropion

N,-butylene--methoxycarbonylphenethylamine (Ritalin)
,3-dihydroxy-N-methylphenethylamine (Sudafed PE)
-methylphenethylamine (Speed,5 Dexedrine,6 Benzedrine Inhalers,7 Adderall,8 Vyvanse9)
N-methylamphetamine (Meth,10 Methedrine, Desoxyn,11 Vick's Vapo Inhalers12)
N-methyl--hydroxyamphetamine (Ephedra,13 Sudafed14)
d--hydroxyamphetamine (Khat15)
-ketoamphetamine (Khat16)
3-chloro-N-tert-butyl--ketoamphetamine (Wellbutrin)

Empathogens:
MDA
MDMA

3,4-methylenedioxyamphetamine (Sally, Tenamfetamine)

3,4-methylenedioxy-N-methylamphetamine (Molly, Ecstasy17)

Psychedelics:18
Mescaline
Escaline
Allylescaline
DOM
DOB
DOC
DOI
2C-B
2C-E
2C-I
25B-NBOMe
25C-NBOMe
25I-NBOMe

3,4,5-trimethoxyphenethylamine (Peyote19)
3,5-dimethoxy-4-ethoxy-phenethylamine
4-allyloxy-3,5-dimethyloxyphenylethylamine
2,5-dimethoxy-4-methylamphetamine (STP)
2,5-dimethoxy-4-bromoamphetamine
2,5-dimethoxy-4-chloroamphetamine
2,5-dimethoxy-4-idoamphetamine
2,5-dimethoxy-4-bromophenethylamine
2,5-dimethoxy-4-ethylphenethylamine
2,5-dimethoxy-4-iodophenethylamine
2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine

The term speed can refer to any combination of L and D isomers of amphetamine or methamphetamine, but classically it refers to the D
isomer of amphetamine.
6
Dexedrine is the D isomer of amphetamine (dextroamphetamine).
7
Benzedrine inhalers contained equal parts D and L isomers of amphetamine.
8
Adderall is 25% racemic amphetamine aspartate monohydrate, 25% racemic amphetamine sulfate, 25% dextroamphetamine saccharate, and
25% dextroamphetamine sulfate.
9
Vyvanse is the brand name for Lisdexamfetamine, a molecule comprised of a dextroamphetamine and L-lysine (as the lysine metabolizes, the
dextroamphetamine is released).
10
Mixtures of D and L isomers of methamphetamine are generally powders, while purer forms of the D or L isomer can be crystals. Relatively
purer crystal forms of the D isomer of methamphetamine (light blue crystal dextromethamphetamine hydrochloride) comprise good street meth
(crystal meth).
11
Methedrine was and Desoxyn is salted dextromethamphetamine (still available in the USA with any doctors prescription). So far as I know,
however, Desoxyn, unlike Methedrine in the 1960s and 1970s, is not available behind the counter in prefilled syringes for direct injection.
12
Vick's Vapo Inhalers contain the L isomer of methamphetamine (levomethamphetamine or Levmetamfetamine), menthol, and camphor.
13
Ephedra contains a variety of different isomers of ephedrine.
14
Sudafed contains an isomer of ephedrine known as pseudo-ephedrine.
15
Cathine is one of the active alkaloids found in khat.
16
Cathinone is one of the active alkaloids found in khat.
17
Pressed ecstasy tablets often contain a mixture of MDMA and other drugs, especially amphetamines (usually, Adderall). True molly is pure
crystal MDMA HCl and is a light brown color (can appear dark brown in single chunks larger than 3g or so).
18
The so-called psychedelic amphetamines are sometimes also quite empathogenic, especially DOB, DOC, 2C-E, and 25C-NBOMe.
19
Mescaline is considered the main active ingredient in peyote.

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Phenethylamine and Its Precursors

Phenethylamine

2-phenylethanamine

L-Tyrosine

4-hydroxyphenylalanine

L-DOPA

L-3,4-dihydroxyphenylalanine

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Phenethylamine Neurotransmitters and Hormones

Dopamine

3,4-dihydroxyphenethylamine

Norepinephrine

,3,4-trihydroxyphenethylamine

Epinephrine

,3,4-trihydroxy-N-methylphenethylamine

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Phenethylamine Stimulants (1/2)

Methylphenidate

N,-butylene--methoxycarbonylphenethylamine

Phenylephrine

,3-dihydroxy-N-methylphenethylamine

Amphetamine

-methylphenethylamne

Methamphetamine

N-methylamphetamine

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Phenethylamine Stimulants (2/2)

Ephedrine

N-methyl--hydroxyamphetamine

Cathine

d--hydroxyamphetamine

Cathinone

-ketoamphetamine

Bupropion

3-chloro-N-tert-butyl--ketoamphetamine

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Phenethylamine Empathogens
MDA

3,4-methylenedioxyamphetamine

MDMA

3,4-methylenedioxy-N-methylamphetamine

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Mescaline and Its Derivatives

Mescaline

3,4,5-trimethoxyphenethylamine

Escaline

3,5-dimethoxy-4-ethoxy-phenethylamine

Allylescaline

4-allyloxy-3,5-dimethyloxyphenylethylamine

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DOx Series a.k.a. Psychedelic Amphetamines

DOM

2,5-dimethoxy-4-methylamphetamine

DOB

2,5-dimethoxy-4-bromoamphetamine

DOC

2,5-dimethoxy-4-chloroamphetamine

DOI

2,5-dimethoxy-4-idoamphetamine

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Phenethylamine 2C-x Series

2C-B

2,5-dimethoxy-4-bromophenethylamine

2C-E

2,5-dimethoxy-4-ethylphenethylamine

2C-I

2,5-dimethoxy-4-iodophenethylamine

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25x-NBOMe Series
25B-NBOMe

2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine

25C-NBOMe

2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine

25I-NBOMe

2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine

Notes:
25I-NBOMe, for example, is made from 2C-I and 2-methoxybenzaldehyde by reductive alkylation.
Thus, NBOMes are N-Benzyl-Oxy-Methyl derivatives on an ethanamine base (thus the term "NBOMe).
In 2003, Ralf Heim first synthesized NBOMes for his Ph.D. thesis in Chemistry at the Freie Universitt Berlin.
Prof. David E. Nichols and his team at Purdue University introduced NBOMes to the USA after reading Heims thesis.
In 2010, NBOMes started becoming available in the USA (and worldwide), via online research chemical vendors.
In 2011, NBOMes started becoming widely available in the USA (and worldwide), via the Darknet.
In 2012, the US State of Virginia officially outlawed NBOMes and their derivates.
In early 2013, the US States of Arkansas, Florida, and Louisiana officially outlawed NBOMes and their derivates.
In late 2013, the US Federal Congress officially scheduled and outlawed NBOMes and their derivatives.

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