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Psychedelic drug
Pharmaceutical compound
DMMDA-2 is a bioactive phenethylamine discussed by Alexander Shulgin in his book PiHKAL (Phenethylamines i Have Known And Loved); however, he was not the first to synthesize it.[1] Shulgin comments in his book that a 50 milligram dose of DMMDA-2 produces similar effects to MDA.[1] DMMDA-2 can be synthesized from dillapiole.[1]
DMMDA-2 is equivalent to 5 mescaline units. DMMDA-2's isomer DMMDA is equivalent to 12 mescaline units.[2]
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| | No ring subs. | |
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| 4-Hydroxytryptamines | |
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| 5-Hydroxytryptamines | |
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| 5-Methoxytryptamines | |
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| Other ring subs. |
- 2,N,N-TMT
- 4,N,N-TMT
- 5-Bromo-DMT
- 5-N,N-TMT
- 7,N,N-TMT
- 5-Fluoro-DMT
- 5-MeO-2,N,N-TMT
- 5-MeO-4,N,N-TMT
- 6-Fluoro-DMT
- Bretisilocin (GM-2505; 5-fluoro-MET)
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| α-Alkyltryptamines | |
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| Others | |
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- Ergolines/lysergamides (e.g., LSD)
- Harmala alkaloids and β-carbolines (e.g., harmine, harmaline)
- Iboga alkaloids (e.g., 18-MAC, 18-MC, coronaridine, ibogaine, ibogamine, ME-18-MC, noribogaine, tabernanthine, voacangine)
- Ibogalogs (e.g., ibogainalog)
- Partial ergolines (e.g., NDTDI, RU-28306, DEIMDHPCA, CT-5252)
- Piperidinylethylindoles (e.g., Pip-T)
- Pyrrolidinylethylindoles (e.g., Pyr-T, 5-MeO-pyr-T)
- Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI)
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- Benzofurans (e.g., 5-MeO-DiBF, dimemebfe (5-MeO-BFE), mebfap)
- Benzothiophenes (e.g., 3-APBT)
- Indazoles (e.g., AL-38022A, O-methyl-AL-34662)
- Indenes (e.g., C-DMT)
- Isotryptamines (e.g., 6-MeO-isoDMT, Ro60-0175)
- MYCO-005
- Quinolinylethylamines (e.g., mefloquine)
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- Others: 2C-G-x (e.g., 2C-G-3, 2C-G-5)
- β-Keto-2C-B (βk-2C-B)
- β-Keto-2C-I (βk-2C-I)
- β-Methyl-2C-B (BMB)
- (e.g., BOB, BOD, BOH-2C-B)
- (e.g., HOT-2, HOT-7, HOT-17)
- N-Ethyl-2C-B
- (e.g., 2CD-2-ETO, 2CD-5-ETO, 2CE-5-ETO, 2CE-5iPrO, 2CT2-5-ETO, ASR-2001 (2CB-5PrO))
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| Others |
- 2-TOET
- 2-TOM
- 25B-NAcPip
- 4-HA
- 5-TOET
- 5-TOM
- Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F-2, F-22)
- Benzothiophenes (e.g., 5-APBT, 6-APBT)
- DMAs (e.g., 2,4-DMA, 3,4-DMA)
- Fenfluramine
- MMA (3-MeO-4-MA)
- Norfenfluramine
- (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA)
- PMA (4-MA)
- (e.g., TMA-3, TMA-4, TMA-5, TMA-6)
- TOMSO
- ZDCM-04
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- 1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline)
- 2-Aminoindanes (e.g., DOM-AI)
- 2-Aminotetralins (e.g., DOM-AT)
- 3-Phenylpiperidines (e.g., LPH-5, LPH-48)
- Benzazepines (e.g., lorcaserin)
- Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline)
- Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
- DMBMPP (juncosamine)
- Ergolines/lysergamides (e.g., LSD)
- Glaucine
- IHCH-7113
- Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA)
- Phenylcyclopropylamines (e.g., DMCPA, TMT)
- Phenylmorpholines (phenmetrazines) (e.g., 2C-B-morpholine)
- Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex)
- Z3517967757
- ZC-B
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| Others | |
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| Natural sources |
- Tryptamines: Acacia spp. (e.g., Acacia acuminata, Acacia confusa)
- Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna), Dipolopterys cabrerana (chaliponga, chacruna), Mimosa tenuiflora (Mimosa hostilis; jurema))
- Brosimum (e.g., Brosimum acutifolium (takini))
- Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene), Anadenanthera colubrina (vilca, cebil))
- Incilius alvarius (Bufo alvarius; Colorado River toad, Sonoran Desert toad; bufo)
- Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis, Psilocybe mexicana (teonanacatl))
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| Phenethylamines | |
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| Amphetamines | |
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| Phentermines | |
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| Cathinones | |
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Phenylisobutylamines
(and further-extended) | |
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Catecholamines
(and close relatives) | |
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Cyclized
phenethylamines | | Phenylalkylpyrrolidines | |
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2-Benzylpiperidines
(phenidates) | |
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Phenylmorpholines
(phenmetrazines) | |
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Phenyloxazolamines
(aminorexes) | |
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Isoquinolines and
tetrahydroisoquinolines | |
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| 2-Aminoindanes | |
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| 2-Aminotetralins | |
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| Others / unsorted |
- 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, jimscaline)
- 2-ADN
- 2-Benzhydrylpyrrolidine
- 3-Benzhydrylmorpholine
- 3-Phenylpiperidines (e.g., 3-phenylpiperidine, OSU-6162 (PNU-96391), LPH-5, LPH-48)
- 6-AB
- AL-1095
- Benzazepines (e.g., fenoldopam, lorcaserin, SCHEMBL5334361)
- Benzocyclobutenes (e.g., 2CBCB-NBOMe, S33005, TCB-2, tomscaline)
- Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
- Butyltolylquinuclidine
- Cypenamine (trans-2-phenylcyclopentylamine)
- Diphenidine
- Diphenylprolinol
- DMBMPP
- Ergolines (e.g., LSD)
- GYKI-52895
- HDMP-29
- Ivabradine
- Lumateperone and analogues (e.g., IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549)
- Methoxphenidine
- Methylmorphenate
- Milnacipran
- MT-45
- 2-Naphthylamine
- Org 6582
- Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, RU-27251)
- PF-592,379
- Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine)
- Tricyclics (e.g., benzoctamine, dizocilpine)
- Z3517967757
- ZC-B
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| Related compounds |
- 2-Furylethylamine
- 2-Pyrrolylethylamine
- 3-Pyrrolylethylamine
- 3-Pyrrolylpropylamine
- 2-Tetrahydrofurylethylamine
- 4-Benzylpiperidine
- 7-AB
- Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane)
- Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline)
- Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide)
- Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine)
- Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine)
- Phenylalkenylamines (e.g., phenylbutenamine)
- Phenylalkynylamines (e.g., phenylbutynamine)
- Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine)
- Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
- Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)
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