PRO-LAD

PRO-LAD
Clinical data
Other names	PRO-LAD,; 6-propyl- 6-nor- Lysergic acid diethylamide,; (6aR,9R)- N,N- diethyl- 7-propyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9- carboxamide
Routes of; administration	Oral
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) ; UK: Under Psychoactive Substances Act ; US: Analogue to a Schedule I/II drug but only if it is intended for human consumption; Illegal in France;
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
	show IUPAC name
CAS Number	65527-63-1 ;
PubChem CID	44457803;
ChemSpider	21106361 ;
ChEMBL	ChEMBL22258 ;
CompTox Dashboard (EPA)	DTXSID50215824 ;
Chemical and physical data
Formula	C22H29N3O
Molar mass	351.494 g·mol−1
3D model (JSmol)	Interactive image;
	show SMILES
	show InChI

PRO-LAD is an analogue of LSD. It is described by Alexander Shulgin in the book TiHKAL. PRO-LAD is a psychedelic drug similar to LSD, and is around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.^[2]

Legal status[]

On June 10, 2014 the UK Advisory Council on the Misuse of Drugs (ACMD) recommended that PRO-LAD be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying it as ever having been sold or any harm associated with its use.^[3] The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014.

PRO-LAD is illegal in Switzerland as of December 2015.^[4]

Literature[]

Hoffman, Andrew J.; Nichols, David E. (1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.
Niwaguchi, T.; Nakahara, Y.; Ishii, H. (1976). "Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds". Yakugaku Zasshi. 96 (5): 673–678. doi:10.1248/yakushi1947.96.5_673. PMID 987200.
Robert C. Pfaff, Xuemei Huang, Danuta Marona-Lewicka, Robert Oberlender and David E. Nichols: Lysergamides Revisited. In: NIDA Research Monograph 146: Hallucinogens: An Update. p. 52, 1994, United States Department of Health and Human Services.

References[]

^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
^ Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–5. doi:10.1021/jm00147a022. PMID 4032428.
^ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.

External links[]

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[1] "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.

[pmid4032428-2] Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–5. doi:10.1021/jm00147a022. PMID 4032428.

[ACMD_tryptamines-3] ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.

[4] "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.

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show v t Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine (Dihydroergonovine, Dihydroergobasine) Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergol Mesulergine Metergoline MIPLA Methysergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA 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 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 CY-208,243 Ergoline Lergotrile Nicergoline Pergolide
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)

PRO-LAD

Contents

Legal status[]

Literature[]

See also[]

References[]

External links[]

Clinical data

Other names	PRO-LAD, 6-propyl- 6-nor- Lysergic acid diethylamide, (6aR,9R)- N,N- diethyl- 7-propyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9- carboxamide
Routes of administration	Oral
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act US: Analogue to a Schedule I/II drug but only if it is intended for human consumption Illegal in France^[1]
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
show IUPAC name (8β)-N,N-Diethyl-6-propyl-9,10-didehydroergoline-8-carboxamide
CAS Number	65527-63-1^Y
PubChem CID	44457803
ChemSpider	21106361^Y
ChEMBL	ChEMBL22258^Y
CompTox Dashboard (EPA)	DTXSID50215824
Chemical and physical data
Formula	C₂₂H₂₉N₃O
Molar mass	351.494 g·mol⁻¹
3D model (JSmol)	Interactive image
show SMILES CCN(CC)C(=O)[C@@H]2C=C1c3cccc4[nH]cc(C[C@H]1N(C2)CCC)c34
show InChI InChI=1S/C22H29N3O/c1-4-10-25-14-16(22(26)24(5-2)6-3)11-18-17-8-7-9-19-21(17)15(13-23-19)12-20(18)25/h7-9,11,13,16,20,23H,4-6,10,12,14H2,1-3H3/t16-,20-/m1/s1^Y Key:HZKYLVLOBYNKKM-OXQOHEQNSA-N^Y