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Saturday, December 19, 2015

The great master list of every hallucinogen that has been available + drug taxonomy

Here's a list I compiled of every hallucinogenic substance within the psychedelic-dissociative-deliriant trifecta. Stimulants, benzos, cannabanoids, alcohol, and plenty others can definitely trigger hallucinations (and so the inclusion of a few unclassifiable things while excluding those might be iffy) but I think the trifecta definition follows rules of what acts on which receptors. (See postscript). There are infinite theoretical compounds that could be included. Thus my criteria for inclusion are ones that are active to some degree and have been available at some point and time on the market beyond Shulgin's labs and personal circle. Pretty much anything with trip reports that aren't from TiHKAL and PiHKAL
This is going to be broken down into incredibly tedious taxonomy like with biology. Not sure if I did that part right, might honestly seem iffy and arbitrary at points. :\ some family names I just gave up and put the name of the chemical because I don't know orgo nomenclature well enough. I guess I'll fix that after I take the class next semester.

If you want a plaintext version with much more simplified pared down classification w/o all that orgo bs its here (it probably needs updating):
http://pastebin.com/AdTJcgKP


PSYCHEDELICS
Phenethylamines
Unsubstituted Phenethylamine family
Phenethylamine
4-DMeO-Phenethylamine family
Lophophine
2,5-DMeO-Phenethylamine (2C-x) family
2C-H
2C-D
2C-E
2C-P
2C-iP
2C-YN
2C-N
2C-T
2C-T-2
2C-T-4
2C-T-7
2C-T-21
2C-C
2C-B
2C-I
2C-TFM
2C-EF
2C-G
2,5-DMeO-Hydroxyphenethylamine family
HOT-7
2,5-DMeO-Bk-phenethylamine family
Bk-2C-B
Bk-2C-I
2,5-DMeO-BOH-phenethylamine family
BOHB
BOHD
2,5-DMeO-BMeO-phenethylamine family
BOD
BOC
BOB
3,5-DMeO-phenethylamine family
Escaline
Proscaline
Cyclopropylmescaline
Allylescaline
Methallylescaline
3,4,5-TMeO-phenethylamine family
Mescaline
2,6-Dichloromescaline
2,6-Dibromomescaline
2,3,6,7-Dihydro-Difuro-phenethylamine family
2C-B-FLY
Amphetamine family
PMA
4-FA
5-IT
5-APDB
5-APB
6-APDB
6-APB
MDA
3-MeO-Amphetamine family
MMA
MMDA
2,5-DMeO-Amphetamine (DOx) family
DOM
DOET
DOPR
DOiP
DON
MEM
DOT (Aleph)
DOT-2 (Aleph-2)
DOF
DOC
DOB
DOI
DOTFM
DOEF
3,5-DMeO-Amphetamine family
3C-E
3C-P
2,4,5-TMeO-Amphetamine family
TMA-2
2,4,6-TMeO-Amphetamine family
TMA-6
Methamphetamine family
PMMA
5-MAPDB
5-MAPB
6-MAPB
MDMA
Ethamphetamine family
MDEA
Hydroxyamphetamine family
MDOH
Cathinone family
Methylone
Ethylone
Butylone
Dibutylone
α-Ethyl 2,5-DMeO Phenethylamine family
4C-D
Bromo-Dragonfly family*
Bromo-Dragonfly
2,5-DMeO-AN family
2C-B-AN
Caffeinated 2,5-DMeO Phenethylamine
ZDCM-04
2,5-DMeO-NBOH family
25C-NBOH
25B-NBOH
25I-NBOH
25E-NBOH
2,5-DMeO-NBOMe family
25H-NBOMe
25D-NBOMe
25E-NBOMe
25P-NBOMe
25iP-NBOMe
25N-NBOMe
25C-NBOMe
25B-NBOMe
25I-NBOMe
25G-NBOMe
25T2-NBOMe
25T7-NBOMe
3,4,5-TMeO-NBOMe family
Mescaline-NBOMe
2,3,6,7-Dihydro-Difuro-NBOMe family
2C-B-FLY-NBOMe
Amphetamine NBOMe family
5-APB-NBOMe
2,5-NBMD family
25I-NBMD
Quinazolinedione NBOme family
RH-34
2-aminoindane family
MEAI
MDAI
2,5-DMeO-BCB-methanamine family
TCB-2
Piperazines
Phenylpiperazine family
pFPP
mCPP
meOPP
TFMPP
Tryptamines
AMT family
AMT
5-MeO-AMT
5-F-AMT
5-Cl-AMT
AET family
AET
5-MeO-AET
NMT family
NMT
4-HO-NMT
4-PO-NMT (Baeocystin)
NET family
NET
DMT family
DMT
4-HO-DMT (Psilocin)
4-AcO-DMT (Psilacetin, acetylpsilocin)
5-HO-DMT (Bufotenin)
5-MeO-DMT
4-Pro-DMT
4-PO-DMT (Psilocybin)
5-Cl-DMT
5-Br-DMT
MET family
MET
4-HO-MET
4-AcO-MET
5-MeO-MET
DET family
DET
4-HO-DET
4-AcO-DET
5-MeO-DET
MPT family
MPT
4-HO-MPT
4-AcO-MPT
5-MeO-MPT
EPT family
EPT
4-HO-EPT
4-AcO-MPT
DPT family
DPT
4-HO-DPT
4-AcO-DPT
5-MeO-DPT
MiPT family
MiPT
4-HO-MiPT
4-MeO-MiPT
4-AcO-MiPT
5-MeO-MiPT
DiPT family
DiPT
4-HO-DiPT
4-AcO-DiPT
5-MeO-DiPT
EiPT family
4-AcO-EiPT
5-MeO-EiPT
PiPT family
PiPT
4-HO-PiPT
MALT family
MALT
4-HO-MALT
4-AcO-MALT
5-MeO-MALT
DALT family
DALT
4-HO-DALT
4-AcO-DALT
5-MeO-DALT
MCPT family
MCPT
4-HO-MCPT
4-AcO-MCPT
DBT family
4-HO-DBT
MPMI family
4-HO-MPMI
TMT family
2-TMT
5-MeO-2-TMT
1-Me-DiPT family
1-Me-5-MeO-DiPT
Tricyclic Tryptamine family
RU-28306
NDTDI
Lysergamide family
LSA
LSH
LSD
ETH-LAD
PRO-LAD
AL-LAD
1cP-AL-LAD
ALD-52
1P-LSD
1P-ETH-LAD
1B-LSD
1cP-LSD
LSZ
LSM
MiPLA
1cP-MiPLA
1P-MiPLA
EiPLA
ECPLA
LAMPA
Benzofurans
Benzofuran Family
5-MeO-BFE
5-MeO-DiBF
Benzazepines
Halogenated Benzazepine family
Lorcaserin


DISSOCIATIVES
Inhalants
Noble Gases
Xenon
Oxides
Nitrous Oxide
Ethers
Diethyl ether
Haloforms
Chloroform
Cyclic Alkanes
Cyclopropane

Diarylethylamines
Diphenylethylamine family
Ephenidine
Isopropylphenidine
2-Chloroephenidine
2-MeO-ephenidine
Diphenyl-pyrrolidine family
Fluorolintane
Diphenylethyl-piperadine family
Diphenidine
Methoxphenidine
Arylcyclohexylamines
PCM family
Deschloroketamine
Hydroxmetamine
Methoxmetamine
Bromoketamine
2F-DCK
2-TFMDCK
Ketamine
Methoxyketamine
PCE family
PCE
3-HO-PCE
3-MeO-PCE
2-OxO-PCE
Methoxetamine
3-Me-2'-Oxo-PCE (DMXE)
N-ethyl-nor-ketamine
3-F-2-Oxo-PCE
PCPr family
3-MeO-PCPr
3-Fl-2'-Oxo-PCPr
MXPr
PCiPr family
MXiPr
PCP family
PCP
4-Me-PCP
4"-Me-PCP
3-Me-PCP
3-HO-PCP
3-MeO-PCP
4-MeO-PCP
3-F-PCP
3-Cl-PCP
PCPy family
PCPy
3-MeO-PCPy
BnCP family
BnCP
PCMo family
3-MeO-PCMo
Alkoxyamine family
PCMEA 
PCEEA
PCMPA
PCHOEA
TCE family
Tiletamine
TCP family
TCP
Indenes
Morpholine-indene family
Indeloxazine
Tricyclics
MK-801 family
MK-801 (Dizocilpine)
Morphinans
Morphinan family
DXO (via DXM)
Adamantanes
Adamantane family
Amantadine
Memantine
Pyrrolidines
HA-966

DELIRIANTS
(No idea how to taxonomize this sorry lol)
Benzhydryls
Diphenylmethoxy family
DPH
Benzhydrylpiperazine family
Cyclizine
Heteroaromatic Benzhydryls
Phenyl-pyridinyl heteroaromatic benzhydryl family (what a mouthful)
Chlorpheniramine
Doxylamine
Hydroxyzine
Phenylpropenes
4-MeO-Phenylpropene family
Myristicin
Elemicin
Indazoles
Benzydamine family
Benzydamine
Cycloheptenes
Cyproheptadine family
Cyproheptadine
Tropane Alkaloids
Atropine family
Atropine
Hyoscyamine
Tricyclo-Tropane family
Scopolamine
Biperiden*
Biperiden family
Biperiden

OTHERS
(these seem to have action on all variety of receptors giving them effects that are qualitatively described as combinations of the other 3 groups)
Muscimol
Mirtazapine
Ibogaine
Voacangine
Glaucine
Cryogenine
Salvinorin A
2-Ethoxymethyl Salvinorin B
2-Methoxymethyl Salvinorin B
Efavirenz
Mefloquine
Grayanotoxin
Ichthyoallyeinotoxins (compound(s) not yet known)

NATURAL SOURCES
(plants containing DMT to be used in ayahuasca admixtures are not included because they need preparation (either to create freebase to smoke or by mixing with an MAOI for oral administration.) All plants included can be consumed with minimal preparation)
Animals
Bufo alvarius (Colorado River Toad/Sonoran Desert Toad)-5-MeO-DMT, Bufotenin
Brachygastra sp. (Honey wasp)(Honey)-Atropine, Scopolamine, Hyoscyamine
Apis dorsata (Himalayan Honeybee)(Honey)-Grayanotoxin
Sarpa salpa (and many other fish)-????
Fungi
Psilocybin Mushrooms (gen. Copelandia, Galerina, Gymnophilus, Inocybe, Mycena, Panaeoulus, Pholiotina, Pluteus & Psilocybe, over 100 species)-Psilocin, Psilocybin, Baeocystin
Dictyonema huaorani - Psilocin, Psilocybin, 5-MeO-DMT, 5-MeO-NMT
Amanita muscaria (Fly Agaric)-Muscimol
Plants
Anadenanthera sp. (Yopo)-5-MeO-DMT, Bufotenin
Argyreia nervosa (Hawaiian Baby Woodrose)-LSA
Ipomoea tricolor (Morning Glory)-LSA
Turbina corymbosa (Ololiuqui)-LSA
Echinopsis Cacti-Mescaline
Lophophora williamsii (Peyote)-Mescaline
Coryphantha macromeris (Donana)-Macromerine
Tabernaemontana undulata (Becchete)-Ibogaine
Tabernanthe iboga (Iboga)-Ibogaine
Voacanga africana-Ibogaine
Salvia divinorum-Salvinorum A
Atropa belladonna (Deadly Nightshade)-Atropine, Scopolamine, Hyoscyamine
Datura sp. (Jimsonweed)-Atropine, Scopolamine, Hyoscyamine
Brugmansia sp. (Angel's Trumpet)-Atropine, Scopolamine, Hyoscyamine
Hyoscyamus niger (Henbane)-Atropine, Scopolamine, Hyoscyamine
Mandragora officinarum (Mandrake)-Atropine, Scopolamine, Hyoscyamine
Myristica sp. (Nutmeg)-Myristicin, Elemicin
Rhododendron sp.-Grayanotoxin
Heimia_salicifolia -Cryogenine

* I really honestly just don't know what to call this structure with regards to cladistics
POSTSCRIPT-
So thus by definition:
Psychedelics primarily act as agonists for some of the 5HT1 and 5HT2 receptors
Dissociatives primarily act as NMDA receptor antagonists
Deliriants primarly act as mACh receptor antagonists
these definitions are nowhere near comprehensive, MDMA for example acts primarily on receptors that identify it as an amphetamine (TAAR1 and VMAT2), but also has slight activity on the 5HT1 & 2 receptors.... classifying them and ordering them was mostly based on structure, taxonomy by receptor is a nightmare... like MDMA acts on similar receptors as amphetamines, while "psychedelic amphetamines" (DOB for example) act on 5-HT2c receptors (along with the main psychedelic ones 5HT2a and 5HT2b) with seemingly little action on the TAAR1 adn VMAT2 receptors, while 2C-B, the non amphetamine version, acts only on 5-HT2c. So what decides the receptor affinity? Is it the 2,5 methoxy groups that 2C-B and DOB share? It certainly doesn't seem to have to do anything with one being an amphetamine, although MDMA shares receptor affinity with other amphetamines? Do those 2,5-MeO groups take priority? Not only that but 2C-B and 2C-T-2 have completely different receptor affinities, the only difference being the active group on the 4 position. What role does this play?? ?????? Maybe these are very basic questions and I just don't know anything about the principles of pharmacology. If anyone knows this better than me (and honestly the place these questions are coming from might be wrong, these might not even be valid questions, I really am not well read on the subject) please tell me

Drug nomenclature is a fucking mess. Sometimes I use the chemical names, sometimes I use common names (I think they're INN names). The tryptamines have a very codified and standardized nomenclature system, while the phenethylamines are a mess. the 2C-x and DOx naming convention do not follow any real system of nomenclature (2C stands for 2 carbons (the 2,5 MeO groups... even though mescaline and analogues also have 2 MeO groups???) and DOx is Dimethoxy-x-amphetamine ???? I love u sasha shulgin but what) but the codified phenethylamine naming system is just a fucking mouthful and while there probably is some more valid abbreviation no one knows it by that (DOM for example, 2,5-dimethoxy-4-methyl-amphetamine could be 2,5,DMeO-4MA x_x nobody calls it that) so for that section I am just using the most common nomenclature. (No one is calling mescaline 3,4,5-TMeO-P lol)
Some other nomenclature oddities-LSD is more appropriately labeled LAD (Lysergic Acid Diethylamide) (the LSD abbreviation comes from its German name). I say appropriately labeled above because all the other chemicals in that family follow the LAD naming convention. Except LSA and 1-P-LSD and ALD-52 and LSM. The use of the LSx and LAx conventions honestly seem arbitrary. Anyone know what's up with that?
Dividing up the arylcyclohexamines was a mess... Ketamine serves as a basis for several compounds, though two seem to be defined by being analogues from editing the fundamental structure of the ketamine molecule...What piece of the ketamine molecule defines it as ketamine? Is it the Cl? The N-methylamine? Why would something lacking the Cl have the suffix ketamine, and why would something with an methyl-n-methylamine instead of n-methylamine also have that suffix? Based on my limited knowledge of orgo I would deduce the des- and nor- suffixes indicate analogues from removal of certain molecules, but couldn't those also be considered analogues of PCM and PCE respectively? who knows :\
Furthermore, tryptamine is a colloquialism, the more proper term would be indole-ethanamine. Tryptamine is derived from tryptophan, the amino acid to which the family bears structural similarity (tryptophan also happens to be a precursor to two members of the tryptamine family, serotonin and melatonin). The name Tryptophan is further derived from the enzyme Trypsin, which comes from the greek root "tripsimo" (rubbing). Not sure why it's called that.
Also I think its interesting how many monotypic clades end up cropping up, even from the "order" level down (eg. the Indazoles (or that should just be indazole I guess)), but this is just within the system of taxonomy for hallucinogens that have been available. Monotypic taxons are a mess but a necessary one and they are essential to keep order in biological cladistics, if anything to show us the absurd degree that biodiversity has attained. For example, Lepidoptera, the order of insects containing butterflies and moths, has 3 monotypic suborders representing some very strange obscure moths only found in little endemic patches of the world. The 4th suborder contains eveyr single other butterfly and moth known. Account for ALL chemical compounds (not even psychoactive ones) and nothing is monotypic anymore. Interesting exercise in cladistics I guess.

3 comments:

  1. "Pretty much anything with trip reports that aren't from TiHKAL and PiHKAL"

    I have a few tens of thousands of trip reports of data analyzed and i need to be able to create an index and categorize them. to identify them i can use the strings above. are you ok with that?

    ReplyDelete
    Replies
    1. Yes! Though I need to go through and update some parts

      Delete
  2. My middle leg, long. My vision, clear.

    ReplyDelete