Chemistry:1B-LSD

1B-LSD
Legal status
Legal status	BR: F2 ; DE: NpSG (Industrial and scientific use only) ; UK: Under Psychoactive Substances Act ; Illegal in France, Italy, Singapore;
Identifiers
	IUPAC name (6aR,9R)-N,N-diethyl-6-methyl-4-butanoyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	2349376-12-9;
PubChem CID	145875086;
ChemSpider	82827098;
UNII	Y6JQX3L6LP;
Chemical and physical data
Formula	C24H31N3O2
Molar mass	393.531 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1[C@](C2=C[C@@H](C(N(CC)CC)=O)C1)([H])CC3=CN(C(CCC)=O)C4=C3C2=CC=C4;
	InChI InChI=1S/C24H31N3O2/c1-5-9-22(28)27-15-16-13-21-19(18-10-8-11-20(27)23(16)18)12-17(14-25(21)4)24(29)26(6-2)7-3/h8,10-12,15,17,21H,5-7,9,13-14H2,1-4H3/t17-,21-/m1/s1; Key:SVRFNPSJPIDUBC-DYESRHJHSA-N;

Short description: Chemical compound

1B-LSD (N1-butyryl-lysergic acid diethylamide) is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug.^[2] In tests on mice it was found to be an active psychedelic, though with only around 1/7 the potency of LSD itself.^[3]^[4]^[5]

Legal status

1B-LSD is illegal in Singapore.^[6] Sweden's public health agency suggested classifying 1B-LSD as a hazardous substance, on June 24, 2019.^[7]

References

↑ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". 20 May 2021. https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554.
↑ "Identification of 1-Butyl-Lysergic Acid Diethylamide (1B-LSD) in Seized Blotter Paper Using an Integrated Workflow of Analytical Techniques and Chemo-Informatics". Molecules 25 (3): 712. February 2020. doi:10.3390/molecules25030712. PMID 32045999.
↑ "In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures". Analytical and Bioanalytical Chemistry 411 (19): 4751–4763. July 2019. doi:10.1007/s00216-018-1558-9. PMID 30617391. http://researchonline.ljmu.ac.uk/id/eprint/9841/13/ABC-01967-2018_02_accepted.pdf.
↑ "Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD)". Drug Testing and Analysis 11 (8): 1122–1133. August 2019. doi:10.1002/dta.2613. PMID 31083768.
↑ "Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD)". Neuropharmacology 172: 107856. August 2020. doi:10.1016/j.neuropharm.2019.107856. PMID 31756337. PMC 9191647. https://researchonline.ljmu.ac.uk/id/eprint/11815/1/NEUROPHARM-D-19-00561R1_accepted_uncorrected.pdf.
↑ "Misuse of Drugs Act - Singapore Statutes Online". https://sso.agc.gov.sg/Act/MDA1973.
↑ "Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 24 June 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/juni/atta-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/.

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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". 20 May 2021. https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554.

[2] "Identification of 1-Butyl-Lysergic Acid Diethylamide (1B-LSD) in Seized Blotter Paper Using an Integrated Workflow of Analytical Techniques and Chemo-Informatics". Molecules 25 (3): 712. February 2020. doi:10.3390/molecules25030712. PMID 32045999.

[3] "In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures". Analytical and Bioanalytical Chemistry 411 (19): 4751–4763. July 2019. doi:10.1007/s00216-018-1558-9. PMID 30617391. http://researchonline.ljmu.ac.uk/id/eprint/9841/13/ABC-01967-2018_02_accepted.pdf.

[4] "Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD)". Drug Testing and Analysis 11 (8): 1122–1133. August 2019. doi:10.1002/dta.2613. PMID 31083768.

[5] "Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD)". Neuropharmacology 172: 107856. August 2020. doi:10.1016/j.neuropharm.2019.107856. PMID 31756337. PMC 9191647. https://researchonline.ljmu.ac.uk/id/eprint/11815/1/NEUROPHARM-D-19-00561R1_accepted_uncorrected.pdf.

[6] "Misuse of Drugs Act - Singapore Statutes Online". https://sso.agc.gov.sg/Act/MDA1973.

[7] "Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 24 June 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/juni/atta-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/.

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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	1B-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergonovine MIPLA MLD-41 PARGY-LAD PRO-LAD
clavines	agroclavine elymoclavine lysergol festuclavine fumigaclavine A fumigaclavine B fumigaclavine C
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)

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Legal status	BR: F2 DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in France,^[1] Italy, Singapore
Identifiers
IUPAC name (6aR,9R)-N,N-diethyl-6-methyl-4-butanoyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number	2349376-12-9
PubChem CID	145875086
ChemSpider	82827098
UNII	Y6JQX3L6LP
Chemical and physical data
Formula	C₂₄H₃₁N₃O₂
Molar mass	393.531 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1[C@](C2=C[C@@H](C(N(CC)CC)=O)C1)([H])CC3=CN(C(CCC)=O)C4=C3C2=CC=C4
InChI InChI=1S/C24H31N3O2/c1-5-9-22(28)27-15-16-13-21-19(18-10-8-11-20(27)23(16)18)12-17(14-25(21)4)24(29)26(6-2)7-3/h8,10-12,15,17,21H,5-7,9,13-14H2,1-4H3/t17-,21-/m1/s1 Key:SVRFNPSJPIDUBC-DYESRHJHSA-N

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