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MPM (drug)

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MPM
Clinical data
Other names4-Propoxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-propoxyamphetamine
Drug classSerotonin 5-HT2 receptor agonist
ATC code
  • None
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 checkY
  • Key:FTJOFRCENIVFLC-UHFFFAOYSA-N checkY
  (verify)

MPM, also known as 2,5-dimethoxy-4-propoxyamphetamine, is a lesser-known putative 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]

MPM produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3] It shows about the same potency as TMA-2 and MEM in this test.[3] In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin gives the dose range as "30 mg or more" and the duration as "probably short".[1] The drug produced weak or threshold effects at doses of 15 to 30 mg.[1][4] 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.[5]

MPM was first described in the scientific literature by Shulgin in 1978.[4] 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]

See also

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References

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  1. ^ a b c d e f MPM entry in PiHKAL on Erowid
  2. ^ a b 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 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.
  4. ^ 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.
  5. ^ 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.
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