MPD-75

Last updated

MPD-75
MPD-75 2D.svg
MPD-75 3D.png
Clinical data
Other namesMPD75; 1-Methyl-N-pyrrolidyllysergamide; 1-Methyllysergic acid pyrrolidide; 1-Methyl-LA-pyrrolidineamide; (1,6-Dimethyl-9,10-didehydroergolin-8β-yl)(pyrrolidin-1-yl)methanone
Routes of
administration 		Oral
Drug class Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • [(6aR,9R)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinolin-9-yl]-pyrrolidin-1-ylmethanone
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H25N3O
Molar mass 335.451 g·mol−1
3D model (JSmol)
  • CN1C[C@@H](C=C2[C@H]1CC3=CN(C4=CC=CC2=C34)C)C(=O)N5CCCC5
  • InChI=1S/C21H25N3O/c1-22-12-14-11-19-17(16-6-5-7-18(22)20(14)16)10-15(13-23(19)2)21(25)24-8-3-4-9-24/h5-7,10,12,15,19H,3-4,8-9,11,13H2,1-2H3/t15-,19-/m1/s1
  • Key:PWISINPCTJKXCA-DNVCBOLYSA-N

MPD-75, also known as 1-methyl-N-pyrrolidyllysergamide or as 1-methyllysergic acid pyrrolidide, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). [1] [2] [3] [4] It is the 1-methyl derivative of lysergic acid pyrrolidide (LA-Pyr; LPD-824) and the N-pyrrolidide analogue of 1-methyl-LSD (MLD-41). [2] Extensive metabolism of other 1-methylated lysergamides to their secondary amine derivatives, for instance methysergide (1-methylmethylergometrine) conversion into methylergometrine, has been observed. [5] [6]

Contents

Use and effects

MPD-75 was evaluated in humans and was found to produce partial LSD-like effects. [2] [3] [4] It was reported to have had a faster onset and shorter duration compared to LSD. [2] MPD-75 showed less than 5% of the potency of LSD in producing LSD-like effects, with a required dose of >20 μg/kg or >1.6 mg orally. [2] [7] [3] [4] According to another source however, MPD-75 had 7% of the potency of LSD in humans. [8] For comparison, LA-Pyr (LPD-824) had approximately 10% of the potency of LSD and had more full LSD-like effects, while 1-methyl-LSD (MLD-41) had 33% of the potency of LSD and likewise produced full LSD-like effects. [2] [3] [4]

Interactions

Pharmacology

Pharmacodynamics

In animal studies, MPD-75 had 4% of the toxicity of LSD in rabbits (presumably in terms of LD50 Tooltip median lethal dose), 0% of its pyretogenic activity in rabbits, and 130% of its antiserotonergic activity in the isolated rat uterus. [8] [9]

History

MPD-75 was first described in the scientific literature by Albert Hofmann and colleagues by 1957. [10] [11] It has not been encountered as a designer drug as of 2020. [10]

See also

References

  1. ↑ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  2. 1 2 3 4 5 6 Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M.
  3. 1 2 3 4 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.
  4. 1 2 3 4 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 / 3. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN   978-3-642-67772-4. OCLC   8130916.
  5. ↑ Majrashi M, Ramesh S, Deruiter J, Mulabagal V, Pondugula S, Clark R, et al. (2017). "Multipotent and Poly-therapeutic Fungal Alkaloids of Claviceps purpurea". In Agrawal DC, Tsay HS, Shyur LF, Wu YC, Wang SY (eds.). Medicinal Plants and Fungi: Recent Advances in Research and Development. Medicinal and Aromatic Plants of the World. Vol. 4. pp. 229–252. doi:10.1007/978-981-10-5978-0_8. ISBN   978-981-10-5977-3. ISSN   2352-6831. Metabolites of methysergide also exhibit pharmacological activity. Methylergometrine (one of methysergide's metabolites) is responsible for methysergide's therapeutic effects regarding migraine treatment (Müller-Schweinitzer and Tapparelli 1986). [...] The systemic availability of methysergide after oral administration is only 13%, due to a high degree of first-pass metabolism by N-1 demethylation to methylergometrine. After oral administration, the plasma concentrations of the metabolite are considerably higher than those of the parent drug, and the area under the plasma concentration curve (AUC) for methylergometrine is more than ten times greater than for methysergide.
  6. ↑ Müller-Schweinitzer E, Tapparelli C (March 1986). "Methylergometrine, an active metabolite of methysergide". Cephalalgia: An International Journal of Headache. 6 (1): 35–41. doi:10.1046/j.1468-2982.1986.0601035.x. PMID   3698092. S2CID   5778173.
  7. ↑ Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Research Monograph. 146: 74–91. PMID   8742795. Archived from the original (PDF) on August 5, 2023.
  8. 1 2 Hoffer A (1965). "D-Lysergic Acid Diethylamide (LSD): A Review of its Present Status". Clinical Pharmacology and Therapeutics. 6 (2): 183–255. doi:10.1002/cpt196562183. PMID   14288188. Archived from the original on 30 March 2025.
  9. ↑ Singh P, Bindal MC, Gupta SP (1 December 1983). "QSAR studies on hallucinogens" . Chemical Reviews. 83 (6): 633–649. doi:10.1021/cr00058a003. ISSN   0009-2665. TABLE XII. Antiserotonin and Hallucinogenic Activities and Hückel's Total MO Energy of LSD and its Analogues [...] Data collected by Kumbar and Siva Sankar,91,92 from ref 70a, 87, 88, and 90; all activities are relative to that of LSD taken as 100.
  10. 1 2 Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, et al. (October 2020). "Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ)". Drug Testing and Analysis. 12 (10): 1514–1521. doi:10.1002/dta.2911. PMC   9191644 . PMID   32803833. Three examples reflecting the C21H25N3O formula (MW 335.45 g/mol) include lysergic acid piperidide (LA-Pip), 1-methyl-N-pyrrolidyllysergamide (MPD-75), and lysergic acid cyclopentylamide (Cepentyl), respectively. Although some chemical and pharmacological descriptions of these three compounds are available (Table S1, Supporting Information), it is unclear whether they are likely to be the focus of future research and/or whether they will appear as new recreational drugs. [...] Table S1. Three examples also reflecting the C21H25N3O formula (Mw 335.45 g/mol) [...] MPD-75 [...]
  11. ↑ Hofmann A, Troxler F (1957). "Substitutionen am Ringsystem der Lysergsäure II. Alkylierung. 44. Mitteilung über Mutterkornalkaloide" . Helvetica Chimica Acta. 40 (6): 1721–1732. doi:10.1002/hlca.19570400620. ISSN   0018-019X . Retrieved 5 June 2025.
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