LSD-Pip

LSD-Pip
Identifiers
	IUPAC name (8β)-6-methyl-8-(piperidin-1-ylcarbonyl)-9,10-didehydroergoline;
CAS Number	50485-23-9 ;
PubChem CID	308707;
ChemSpider	35303396;
UNII	CKN3AJ58H9;
CompTox Dashboard (EPA)	DTXSID20308999 ;
Chemical and physical data
Formula	C21H25N3O
Molar mass	335.451 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4c3c2ccc4)C(=O)N5CCCCC5;
	InChI InChI=1S/C21H25N3O/c1-23-13-15(21(25)24-8-3-2-4-9-24)10-17-16-6-5-7-18-20(16)14(12-22-18)11-19(17)23/h5-7,10,12,15,19,22H,2-4,8-9,11,13H2,1H3/t15-,19-/m1/s1; Key:URDULHYODQAQTM-DNVCBOLYSA-N;
	(verify)

LSD-Pip is a compound from the ergoline family, related to LSD but with the N,N-diethyl substitution replaced by a piperidine group. It is more potent than the corresponding pyrrolidine and morpholine analogues (LPD-824 and LSM-775 respectively), but is still several times less potent than LSD as a 5-HT_2A agonist.^[1] Early studies suggested this compound to be inactive as a psychedelic in humans,^[2] though this does not seem to have been confirmed by any more recent work.

References

^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
^ Cerletti A, Doepfner W (January 1958). "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics. 122 (1): 124–36. PMID 13502837.

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[1] Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.

[pmid13502837-2] Cerletti A, Doepfner W (January 1958). "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics. 122 (1): 124–36. PMID 13502837.

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v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

See also

References