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;
Chemical and physical data
Formula	C21H25N3O
Molar mass	335.442 g/mol
3D model (Jmol)	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[edit]

^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
^ 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] Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.

[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.

[1]

[2]

v t e Ergolines

Lysergic acid derivatives	2-Bromo-LSD (BOL-148) 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 Ergotamine Ergotoxine Ergovaline Lisuride LSD LSH Lysergic Acid Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Pergolide Syntometrine

Psychedelic lysergamides	1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 Ergonovine ETH-LAD IP-LAD LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergonovine Methylisopropyllysergamide MLD-41 PARGY-LAD PRO-LAD

Other ergolines	Ergoline

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)

LSD-Pip

See also[edit]

References[edit]

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Identifiers

IUPAC name (8β)-6-methyl-8-(piperidin-1-ylcarbonyl)-9,10-didehydroergoline
CAS Number	50485-23-9^Y
PubChem CID	308707
ChemSpider	35303396
Chemical and physical data
Formula	C₂₁H₂₅N₃O
Molar mass	335.442 g/mol
3D model (Jmol)	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)