{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = MPD-75.svg | image_class = skin-invert-image | width = 165px
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral | class = Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
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<!-- Identifiers --> | CAS_number = 7221-79-6 | CAS_supplemental = | PubChem = 201987 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 174911 | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = MPD75; 1-Methyl-''N''-pyrrolidyllysergamide; 1-Methyllysergic acid pyrrolidide; 1-Methyl-LA-pyrrolidineamide; (1,6-Dimethyl-9,10-didehydroergolin-8β-yl)(pyrrolidin-1-yl)methanone
<!-- Chemical data --> | IUPAC_name = [(6''aR'',9''R'')-4,7-dimethyl-6,6''a'',8,9-tetrahydroindolo[4,3-fg]quinolin-9-yl]-pyrrolidin-1-ylmethanone | C=21 | H=25 | N=3 | O=1 | SMILES = CN1C[C@@H](C=C2[C@H]1CC3=CN(C4=CC=CC2=C34)C)C(=O)N5CCCC5 | StdInChI = 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 | StdInChIKey = 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).<ref name="TiHKAL">{{CiteTiHKAL }}</ref><ref name="Brimblecombe_1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | title = Hallucinogenic Agents | location = Bristol | pages = 98–144 | date = 1975 | publisher = Wright-Scientechnica | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=69 }}</ref><ref name="Shulgin_2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 }}</ref><ref name="Shulgin_1982">{{cite book | vauthors = Shulgin AT | veditors = Hoffmeister F, Stille G | chapter = Chemistry of Psychotomimetics | title = Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs | location = Berlin | volume = 55 / 3 | pages = 3–29 | date = 1982 | doi = 10.1007/978-3-642-67770-0_1 | series = Handbook of Experimental Pharmacology | publisher = Springer Berlin Heidelberg | isbn = 978-3-642-67772-4 | oclc = 8130916 | url = https://books.google.com/books?id=mrT8CAAAQBAJ | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1 }}</ref> 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).<ref name="Brimblecombe_1975" /> Extensive metabolism of other 1-methylated lysergamides to their secondary amine derivatives, for instance methysergide (1-methylmethylergometrine) conversion into methylergometrine, has been observed.<ref name="MajrashiRamesh2017">{{cite book| vauthors = Majrashi M, Ramesh S, Deruiter J, Mulabagal V, Pondugula S, Clark R, Dhanasekaran M | chapter = Multipotent and Poly-therapeutic Fungal Alkaloids of Claviceps purpurea | veditors = Agrawal DC, Tsay HS, Shyur LF, Wu YC, Wang SY | title = Medicinal Plants and Fungi: Recent Advances in Research and Development | series = Medicinal and Aromatic Plants of the World | volume = 4 | year = 2017 | pages = 229–252 | issn = 2352-6831 | doi = 10.1007/978-981-10-5978-0_8 | isbn = 978-981-10-5977-3 | quote = 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.}}</ref><ref name="Müller-SchweinitzerTapparelli1986">{{cite journal | vauthors = Müller-Schweinitzer E, Tapparelli C | title = Methylergometrine, an active metabolite of methysergide | journal = Cephalalgia: An International Journal of Headache | volume = 6 | issue = 1 | pages = 35–41 | date = March 1986 | pmid = 3698092 | doi = 10.1046/j.1468-2982.1986.0601035.x | s2cid = 5778173 }}</ref>
==Use and effects== MPD-75 was evaluated in humans and was found to produce partial LSD-like effects.<ref name="Brimblecombe_1975" /><ref name="Shulgin_2003" /><ref name="Shulgin_1982" /> It was reported to have had a faster onset and shorter duration compared to LSD.<ref name="Brimblecombe_1975" /> MPD-75 showed less than 5% of the potency of LSD in producing LSD-like effects, with a required dose of >20{{nbsp}}μg/kg or >1.6{{nbsp}}mg orally.<ref name="Brimblecombe_1975" /><ref name="Jacob_1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Research Monograph | volume = 146 | pages = 74–91 | date = 1994 | pmid = 8742795 | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 | archive-url = https://web.archive.org/web/20230805004551/https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 | url-status = dead | archive-date = August 5, 2023 }}</ref><ref name="Shulgin_2003" /><ref name="Shulgin_1982" /> According to another source however, MPD-75 had 7% of the potency of LSD in humans.<ref name="Hoffer_1965" /> 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.<ref name="Brimblecombe_1975" /><ref name="Shulgin_2003" /><ref name="Shulgin_1982" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== In animal studies, MPD-75 had 4% of the toxicity of LSD in rabbits (presumably in terms of {{Abbrlink|LD<sub>50</sub>|median lethal dose}}), 0% of its pyretogenic activity in rabbits, and 130% of its antiserotonergic activity in the isolated rat uterus.<ref name="Hoffer_1965">{{cite journal | vauthors = Hoffer A | title = D-Lysergic Acid Diethylamide (LSD): A Review of its Present Status | journal = Clinical Pharmacology and Therapeutics | volume = 6 | issue = 2 | pages = 183–255 | date = 1965 | pmid = 14288188 | doi = 10.1002/cpt196562183 | url = https://bibliography.maps.org/resources/download/2117 | archive-url = https://web.archive.org/web/20250330030934/https://bibliography.maps.org/resources/download/2117 | archive-date = 30 March 2025 | url-access = subscription }}</ref><ref name="Singh_1983">{{cite journal | vauthors = Singh P, Bindal MC, Gupta SP | title = QSAR studies on hallucinogens | journal = Chemical Reviews | volume = 83 | issue = 6 | pages = 633–649 | date = 1 December 1983 | doi = 10.1021/cr00058a003 | issn = 0009-2665 | url = https://pubs.acs.org/doi/abs/10.1021/cr00058a003 | quote = 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. | url-access = subscription }}</ref>
==History== MPD-75 was first described in the scientific literature by Albert Hofmann and colleagues by 1957.<ref name="Brandt_2020">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Halberstadt AL | title = Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ) | journal = Drug Testing and Analysis | volume = 12 | issue = 10 | pages = 1514–1521 | date = October 2020 | pmid = 32803833 | pmc = 9191644 | doi = 10.1002/dta.2911 | quote = 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 [...] }}</ref><ref name="Hofmann_1957">{{cite journal | vauthors = Hofmann A, Troxler F | title = Substitutionen am Ringsystem der Lysergsäure II. Alkylierung. 44. Mitteilung über Mutterkornalkaloide | journal = Helvetica Chimica Acta | volume = 40 | issue = 6 | pages = 1721–1732 | date = 1957 | doi = 10.1002/hlca.19570400620 | issn = 0018-019X | url = https://onlinelibrary.wiley.com/doi/10.1002/hlca.19570400620 | access-date = 5 June 2025 | url-access = subscription }}</ref> It has not been encountered as a designer drug as of 2020.<ref name="Brandt_2020" />
==See also== * Substituted lysergamide * Lysergic acid pyrrolidide (LA-Pyr; LPD-824) * MLD-41 (1-methyl-LSD) * MLA-74 (1-methyl-LAE)
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5342 MPD-75 - Isomer Design]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Ergolines}}
Category:Methyl compounds Category:Psychedelic lysergamides Category:1-Pyrrolidinyl compounds Category:Serotonin receptor modulators