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double-solid/shaded bond of cyclohexane and cyclopentane of LSD-pip as rendered in Marvin Beans, molecular comparison of LSD with LSD-pip (both rendered with same chemistry-molecular-drawing program)
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'''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-HT2A receptor|5-HT<sub>2A</sub>]] [[agonist]].<ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</ref> Early studies suggested this compound to be inactive as a [[Psychedelic_drug|psychedelic]] in humans,<ref name="pmid13502837">{{cite journal |author=CERLETTI A, DOEPFNER W |title=Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=122 |issue=1 |pages=124–36 |date=January 1958 |pmid=13502837 |doi= |url=}}</ref> though this does not seem to have been confirmed by any more recent work.
'''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-HT2A receptor|5-HT<sub>2A</sub>]] [[agonist]].<ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</ref> Early studies suggested this compound to be inactive as a [[Psychedelic_drug|psychedelic]] in humans,<ref name="pmid13502837">{{cite journal |author=CERLETTI A, DOEPFNER W |title=Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=122 |issue=1 |pages=124–36 |date=January 1958 |pmid=13502837 |doi= |url=}}</ref> though this does not seem to have been confirmed by any more recent work.
{{multiple image

| align = center
| image1 = Lysergic acid diethylamide Marvin Beans Rendered.png
| width1 = 195
| image2 = LSD-Pip Marvin Beans Rendered.png
| width2 = 220
| footer_align = center
| footer = LSD (left) and LSD-Pip (right)
}}


==See also==
==See also==

Revision as of 01:47, 3 March 2016

LSD-Pip
Identifiers
  • (8β)-6-methyl-8-(piperidin-1-ylcarbonyl)-9,10-didehydroergoline
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H25N3O
Molar mass335.442 g/mol g·mol−1
3D model (JSmol)
  • CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4c3c2ccc4)C(=O)N5CCCCC5
  • 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-HT2A 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.

LSD (left) and LSD-Pip (right)

See also


References

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