DMMDA-2

DMMDA-2
Clinical data
Other names2,3-Dimethoxy-4,5-methylenedioxyamphetamine; 5,6-Dimethoxy-MDA; 3,4-Methylenedioxy-5,6-dimethoxyamphetamine; 5,6-Dimethoxy-3,4-methylenedioxyamphetamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen; Serotonin releasing agent
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO4
Molar mass239.271 g·mol−1
3D model (JSmol)
Melting point178 to 180 °C (352 to 356 °F)
  • CC(N)Cc1cc2OCOc2c(OC)c1OC
  • InChI=1S/C12H17NO4/c1-7(13)4-8-5-9-11(17-6-16-9)12(15-3)10(8)14-2/h5,7H,4,6,13H2,1-3H3 Y
  • Key:UQXNREZPUUGSKM-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

DMMDA-2, also known as 2,3-dimethoxy-4,5-methylenedioxyamphetamine or as 5,6-dimethoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to MDA.[1] It is the derivative of MDA with methoxy groups at the 5 and 6 positions and of MMDA and MMDA-2 with an additional methoxy group at either of these positions.[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DMMDA-2's dose as about 50 mg orally and its duration as unknown.[1] Threshold effects are said to occur at a dose of 28 mg (~0.4 mg/kg) or 30 to 50 mg orally.[1][2][3] In earlier publications, Shulgin listed its dose range as approximately 0.6 to 1 mg/kg (or ~42–70 mg for a 70-kg person) orally.[3][4][5] In a subsequent publication, he listed its dose as greater than 50 mg orally.[6]

Information on the properties and effects of DMMDA-2 in humans is sparse and its specific effects were not described, but it has been said to be "much like MDA" and to have similar effects as DMMDA.[1][2][7][3] The effects of DMMDA and DMMDA-2 may reportedly be different from those of other related psychedelics like mescaline, MMDA, and MMDA-2.[7][3] DMMDA-2 has approximately 5 times the potency of mescaline.[1][3][8][4][5][2][9][10] It is more potent than MDA but less potent than DMMDA.[6][5][10][1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

DMMDA-2 showed reduced albeit significant activity as a serotonin releasing agent compared to certain related compounds like MDA and MMDA.[11] It showed no activity as a dopamine releasing agent, in contrast to MDA but similarly to MMDA and MMDA-2.[11] Whereas DMMDA-2 significantly induced serotonin release, MMDA-2 was inactive in terms of serotonin and dopamine release induction.[11]

Chemistry

Synthesis

The chemical synthesis of DMMDA-2 has been described.[1][3] It can be synthesized from dillapiole.[1][3]

Analogues

A variety of positional isomers of DMMDA-2 are possible and/or known, such as DMMDA among others.[1] Other analogues of DMMDA-2 are also known, such as MMDA-2 among others.[1]

History

DMMDA-2 was first described in the scientific literature by Alexander Shulgin and colleagues in 1967.[3][12][8][13][14] However, Shulgin did not synthesize or test it himself.[1] Subsequently, the drug was described in greater detail by Shulgin in PiHKAL in 1991.[1]

Society and culture

DMMDA-2 is a controlled substance in Canada under phenethylamine blanket-ban language.[15]

See also

References

  1. ^ a b c d e f g h i j k l m n o Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ a b c Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.2.11. 2,3-Dimethoxy-4,5-methylenedioxyphenylisopropylamine The second of the isomers that has been studied in man is 2,3-dimethoxy-4,5-methylevedioxyphenylisopropylamine (58, DMMDA-2, 2,3-dimethoxy-4,5-methylenedioxyamphetamine). Its substitution pattern is that of the essential oil dillapiole, a major component of dill oil. Limited clinical trials have shown that threshold responses are elicited by the oral administration of 30–50 mg of the amine hydrochloride (Shulgin and Sargent, 1967) with the prodromal indicators of an intoxication similar to that of MDA. If the effective dose proves to be twice this, DMMDA-2 may be quantitatively ranked as having about five times the potency of mescaline. Neither of the dimethoxymethyledioxyphenylisopropylamines has been studied metaboli-cally.
  3. ^ a b c d e f g h Shulgin AT, Sargent T (September 1967). "Psychotrophic phenylisopropylamines derived from apiole and dillapiole". Nature. 215 (5109): 1494–1495. Bibcode:1967Natur.215.1494S. doi:10.1038/2151494b0. PMID 4861200. Archived from the original on 2025-07-12.
  4. ^ a b Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46–58. PMID 4576313. Archived from the original on 2025-07-12.
  5. ^ a b c Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. Only three methylenedioxy compounds that are not trisubstituted have been studied in man. One is 3,4-methylenedioxyphenylisopropylamine [MDA (LXXIX)]. This compound is not particularly potent (typical dosage, some 120 mg or about three times the activity of mescaline), but its apparent consistency of action has led to its clinical study (Naranjo et al., 1967). The 2,3-isomer is unknown. The remaining two are the dimethoxy derivatives, 2,5-dimethoxy-3,4-methylenedioxyphenylisopropylamine DMMDA (LXXX) and 2,3-dimethoxy-4,5-methylenedioxyphenylisopropylamine DMMDA-2 (LXXXI). They are active at 30 and 70 mg, respectively (Shulgin and Sargent, 1967), corresponding to twelve times and five times the potency of mescaline. These data are presented in Table V.
  6. ^ a b Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
  7. ^ a b Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97 (66–67). Archived from the original on 27 May 2025. Retrieved 31 May 2025. Most of these compounds produce a typical mescaline syndrome, particularly of closed-eye imagery (Shulgin, Sargent, and Naranjo, 1973), in contrast to that produced by tetrasubstituted derivatives such as 2,5-dimethoxy-3,4-methylenedioxyamphetamine [(DMMDA)] (3.22) and 2,3-dimethoxy-4,5-methylenedioxyamphetamine [(DMMDA-2)] (3.23) (Shulgin and Sargent, 1967). These latter two compounds are considered to be different from the true hallucinogenic amphetamines, producing mild perceptual distortion, increased emotional affect and empathy, together with euphoria and lack of anxiety. They also differ from compounds like mescaline and the trimethoxyamphetamines in not producing autonomic distress prior to the onset of intoxication, although mild incoordination has been noted in man. 3,4-Methylenedioxy-amphetamine [(MDA)] also seems atypical and has been suggested as a useful adjunct to psychotherapy (Naranjo, Shulgin, and Sargent, 1967); it enhances intellectual and emotional thinking, together with an increase in the level of fluency and attention, at dose levels less than those required for the appearance of imagery and perceptual distortion (Thiessen and Cook, 1973).
  8. ^ a b Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure–activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297. Archived from the original on 2025-07-12.
  9. ^ Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
  10. ^ a b Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
  11. ^ a b c McKenna DJ, Guan XM, Shulgin AT (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacol Biochem Behav. 38 (3): 505–512. doi:10.1016/0091-3057(91)90005-m. PMID 1829838. Archived from the original on 2025-07-13.
  12. ^ Alexander T. Shulgin, Thornton Sargent, Claudio Naranjo (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines". In Efron DH, Holmstedt B, Kline NS (eds.). Ethnopharmacologic Search for Psychoactive Drugs: Proceedings of a Symposium Held in San Francisco, California, January 28–30, 1967. New York: Raven Press. pp. 202–214. ISBN 978-0-89004-047-8. OCLC 14498182. OL 14623132M. Archived from the original on 12 July 2025.
  13. ^ Shulgin AT (1969). "Psychotomimetic Agents Related to the Catecholamines". Journal of Psychedelic Drugs. 2 (2): 14–19. doi:10.1080/02791072.1969.10524409. ISSN 0022-393X. Archived from the original on 2025-07-12.
  14. ^ Shulgin A (1970). "Chemistry and Structure-Activity Relationships of the Psychotomimetics". In Efron DH (ed.). Psychotomimetic Drugs: Proceedings of a Workshop Organized by the Pharmacology Section, Psychopharmacology Research Branch, National Institute of Mental Health. New York: Raven Press. pp. 21–41. ISBN 9780911216073. OCLC 58755. Archived from the original on 12 July 2025.
  15. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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