MPM (drug)

MPM
Clinical data
Other names4-Propoxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-propoxyamphetamine; TMA2-4-PrO
Routes of
administration		Oral[1]
Drug classSerotonin 5-HT2 receptor agonist
ATC code
  • None
Pharmacokinetic data
Duration of action"Probably short"[1]
Identifiers
  • 1-(2,5-dimethoxy-4-propoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO3
Molar mass253.342 g·mol−1
3D model (JSmol)
  • COc1cc(OC)c(cc1OCCC)CC(C)N
  • InChI=1S/C14H23NO3/c1-5-6-18-14-8-11(7-10(2)15)12(16-3)9-13(14)17-4/h8-10H,5-7,15H2,1-4H3 Y
  • Key:FTJOFRCENIVFLC-UHFFFAOYSA-N Y
  (verify)

MPM, also known as 2,5-dimethoxy-4-propoxyamphetamine or as TMA2-4-PrO, is a possible psychedelic drug of the phenethylamine, amphetamine, and DOx families.[1][2] It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended.[1] The drug is also the α-methyl or amphetamine analogue of 2C-O-7.[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MPM's dose range as 30 mg or more orally and its duration as "probably short".[1] The drug produced weak or threshold effects at doses of 15 to 30 mg.[1][3] In another publication, Shulgin estimated an effective dose of MPM to be around 50 mg and the drug as being around half as potent as TMA-2 or MEM.[4]

Interactions

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

Pharmacology

Pharmacodynamics

MPM produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[5] It shows about the same potency as TMA-2 and MEM in this test.[5]

Chemistry

Synthesis

The chemical synthesis of MPM has been described.[1]

Analogues

Analogues of MPM include TMA-2, MEM, MIPM, MALM, MBM, and MAM, among others.[1][2]

History

MPM was first described in the scientific literature by Shulgin in 1978.[3] Subsequently, Shulgin described the drug in more detail in his book PiHKAL.[1] The compound's name is said to derive from its benzene ring substituents, "methoxy propoxy methoxy".[2]

Society and culture

Canada

MPM is a controlled substance in Canada under phenethylamine blanket-ban language.[6]

See also

References

  1. ^ a b c d e f g h i j MPM entry in PiHKAL on Erowid
  2. ^ a b c Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Frontiers in Pharmacology. 10: 1423. doi:10.3389/fphar.2019.01423. PMC 6893898. PMID 31849671.
  3. ^ a b 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. 3.3.5. 4-(n)-Propoxy-2,5-dimethoxyphenylisopropylamine An unpublished study of the 4-propoxy homolog of TMA-2 (63, 4-(n)-propoxy-2,5-dimethoxyphenylisopropylamine, MPM, 4-(n)-propoxy-2,5-dimethoxyamphetamine) indicates that it has threshold activity at an oral dose level of about 15 mg, as the hydrochloride. It is then approximately as effective, certainly not much less so, than the two lower homologs MEM (60) and TMA-2 (34). The two higher homologs, 4-(n)-butoxy-2,5-dimethoxyphenylisopropylamine and 4-(n)-amyloxy-2,5-dimethoxyphenylisopropylamine (MBM and MAM, respectively) were without any central effects at similar dosages (12 and 16 mg, respectively, orally, as the hydrochloride salts). Too little is known of this homologous series at the present time to generalize as to structure-activity relationships.
  4. ^ Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline Analogs: Substitutions at the 4-Position" (PDF). In Barnett G, Trsic M, Willette RE (eds.). QuaSAR: Quantitative Structure Activity Relationships Of Analgesics, Narcotic Antagonists, And Hallucinogens (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 22. National Institute on Drug Abuse. pp. 27–37. PMID 101882.
  5. ^ a b Halberstadt AL, Chatha M, Chapman SJ, Brandt SD (March 2019). "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice". J Psychopharmacol. 33 (3): 406–414. doi:10.1177/0269881119826610. PMC 6848748. PMID 30789291.
  6. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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