From Wikipedia, the free encyclopedia
DMCPA
|
|
Names
|
Preferred IUPAC name
2-(2,5-Dimethoxy-4-methylphenyl)cyclopropan-1-amine
|
Identifiers
|
|
|
|
|
ChEMBL
|
|
ChemSpider
|
|
|
|
UNII
|
|
|
|
InChI=1S/C12H17NO2/c1-7-4-12(15-3)9(6-11(7)14-2)8-5-10(8)13/h4,6,8,10H,5,13H2,1-3H3 YKey: HYVPPECPQRBJEQ-UHFFFAOYSA-N YInChI=1/C12H17NO2/c1-7-4-12(15-3)9(6-11(7)14-2)8-5-10(8)13/h4,6,8,10H,5,13H2,1-3H3 Key: HYVPPECPQRBJEQ-UHFFFAOYAN
|
O(c1c(cc(OC)c(c1)C2CC2N)C)C
|
Properties
|
|
C12H17NO2
|
Molar mass
|
207.273 g·mol−1
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Chemical compound
2,5-Dimethoxy-4-methylphenylcyclopropylamine (DMCPA) is a lesser-known psychedelic drug and a substituted amphetamine and phenylcyclopropylamine. DMCPA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 15–20 mg and the duration is listed as 4–8 hours.[1] DMCPA produces open-eye visuals, anorexia, and psychedelic dreams.[1] Shulgin gives it a +++ on the Shulgin Rating Scale.[1]
Very little data exists about the pharmacological properties, metabolism, and toxicity of DMCPA.
This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[2]
|
---|
| No ring subs. | |
---|
4-Hydroxytryptamines | |
---|
5-Hydroxytryptamines | |
---|
5-Methoxytryptamines | |
---|
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)
|
---|
α-Alkyltryptamines | |
---|
Others | |
---|
|
- 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)
|
---|
|
- 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)
|
---|
|
---|
| | |
---|
|
- 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))
|
---|
| |
---|
| |
---|
| |
---|
| |
---|
| |
---|
| |
---|
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
|
---|
|
- 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
|
---|
|
---|
| |
---|
Others | |
---|
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))
|
---|
|
|
---|
Phenethylamines | |
---|
Amphetamines | |
---|
Phentermines | |
---|
Cathinones | |
---|
Phenylisobutylamines (and further-extended) | |
---|
Catecholamines (and close relatives) | |
---|
Cyclized phenethylamines | Phenylalkylpyrrolidines | |
---|
2-Benzylpiperidines (phenidates) | |
---|
Phenylmorpholines (phenmetrazines) | |
---|
Phenyloxazolamines (aminorexes) | |
---|
Isoquinolines and tetrahydroisoquinolines | |
---|
2-Aminoindanes | |
---|
2-Aminotetralins | |
---|
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
|
---|
|
---|
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)
|
---|
|