1H-LSD

1H-LSD
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; US: Unscheduled (may be covered by the Federal Analogue Act if sold for human consumption); UN: Unscheduled;
Identifiers
	IUPAC name (6aR,9R)-N,N-diethyl-6-methyl-4-hexanoyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
PubChem CID	170763690;
Chemical and physical data
Formula	C26H35N3O2
Molar mass	421.585 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CC(C=C2[C@H]1Cc1cn(C(=O)CCCCC)c3cccc2c31)C(=O)N(CC)CC;
	InChI InChI=InChI=1S/C26H35N3O2/c1-5-8-9-13-24(30)29-17-18-15-23-21(20-11-10-12-22(29)25(18)20)14-19(16-27(23)4)26(31)28(6-2)7-3/h10-12,14,17,19,23H,5-9,13,15-16H2,1-4H3/t19?,23-/m1/s1; Key:RSBBZALMPUUEKF-LEQGEALCSA-N;

1H-LSD (N1-hexanoyl-lysergic acid diethylamide, SYN-L-027)^[1] is an acylated derivative of lysergic acid diethylamide (LSD), with a six carbon hexanoyl chain attached to the N1 position. It acts as a prodrug for LSD, and in animal studies produces drug-appropriate responding with a similar potency to short-chain homologues such as ALD-52 and 1P-LSD, in contrast to the 4 and 5 carbon homologues 1B-LSD and 1V-LSD which are several times weaker.^[2]

References

^ WO 2024028495, Stratford A, Williamson JP, "Prodrugs of Substituted Ergolines", published 8 February 2024, assigned to Synex Holdings BV
^ Brandt SD, Kavanagh PV, Gare S, Stratford A, Halberstadt AL (July 2024). "Analytical and behavioral characterization of 1-hexanoyl-LSD (1H-LSD)" (PDF). Drug Testing and Analysis. doi:10.1002/dta.3767. PMID 38965834.

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[1] WO 2024028495, Stratford A, Williamson JP, "Prodrugs of Substituted Ergolines", published 8 February 2024, assigned to Synex Holdings BV

[pmid38965834-2] Brandt SD, Kavanagh PV, Gare S, Stratford A, Halberstadt AL (July 2024). "Analytical and behavioral characterization of 1-hexanoyl-LSD (1H-LSD)" (PDF). Drug Testing and Analysis. doi:10.1002/dta.3767. PMID 38965834.

[1]

[2]

v t e Ergolines
Ergolines (incl. lysergines)	13-Fluorolysergol Acetergamine Brazergoline Bromerguride (2-bromolisuride) Cianergoline Delergotrile Descarboxylysergic acid Dihydrolysergic acid Disulergine Dosergoside Ergolene Ergoline Etisulergine Lergotrile Lisuride Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mesulergine Metergoline Nicergoline Pergolide Pibocin B Proterguride Romergoline Sergolexole Terguride Tiomergine
Clavines (6,8-dimethylergolines)	6,8-Dimethylergoline (clavine) 9-Deacetoxyfumigaclavine C Agroclavine Costaclavin Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Penniclavine Setoclavine Partial ergolines and related: Chanoclavine Chanoclavine II Cycloclavine Paliclavine
Lysergamides (lysergic acid amides)	Non-hallucinogenic lysergamides: 1P-BOL-148 2-Bromo-LSD (bromolysergide; BOL-148) 2-Iodo-LSD 12-Hydroxy-LSD 12-Methoxy-LSD Amesergide Cabergoline Ergometrinine isoLSD LY-215,840 Lysergic acid cyclobutylamide (LAcB) Lysergic acid cyclopentylamide (cepentil; LCyP) MBL-61 (2-bromo-1-methyl-LSD) Psychedelic lysergamides: 1B-LSD 1cP-AL-LAD 1cP-LSD 1D-LSD 1DD-LSD 1H-LSD 1P-AL-LAD 1P-ETH-LAD 1P-LSD 1P-MIPLA 1S-LSD 1T-AL-LAD 1T-LSD 1V-LSD AL-LAD ALA-10 (1-acetyl-LAE) ALD-52 (1-acetyl-LSD) BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) Dipropyllysergamide (DPL) Ergine (lysergic acid amide; LSA; LA-111; lysergamide) Ergometrine (ergonovine, ergobasine) ETH-LAD Ethylcyclopropyllysergamide (ECPLA) Ethylisopropyllysergamide (EIPLA) Ethylpropyllysergamide (EPLA; LEP-57) Ethyltrifluoroethyllysergamide (ETFELA) IP-LAD Isoergine (isolysergic acid amide; iso-LSA; iso-LA; isolysergamide) Methylpropyllysergamide (LAMPA) Lysergic acid diethylamide (LSD; lysergide) Lysergic acid ethylamide (LAE-32, LAE) Lysergic acid hydroxyethylamide (LSH) Lysergic acid morpholide (LSM-775) Lysergic acid pyrrolidine (LPD-824) Lysergic acid 2-butylamide (LSB) Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) Lysergic acid 3-pentylamide (LSP) Methylergometrine (methylergonovine, methylergobasine; Methergine) Methylisopropyllysergamide (MIPLA) Methysergide (1-methylmethylergonovine; UML-491) MLA-74 (1-methyl-LAE) MLD-41 (1-methyl-LSD) MPD-75 (1-methyllysergic acid pyrrolidide) OML-632 (1-hydroxymethyl-LSD) PARGY-LAD PRO-LAD Unsorted lysergamides: 13-Fluoro-LSD 13-Hydroxy-LSD 14-Hydroxy-LSD CE-LAD Dihydroergometrine (dihydroergonovine, dihydroergobasine) FLUORETH-LAD Lysergic acid azepane (LSD-Azepane) Lysergic acid ethyl-2-hydroxyethylamide (LEO) Lysergic acid isopropylamide (LAiP) Lysergic acid piperidine (LSD-Pip) Lysergic acid tert-butylamide (LAtB) Propisergide (1-methylergonovine)
Ergopeptines (peptide ergolines)	Bromocriptine Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergosine Dihydroergotamine Epicriptine Ergocornine Ergocristine Ergocryptine Ergoloid (dihydroergotoxine; Hydergine) Ergonine Ergosine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Mergocriptine Metergotamine
Partial ergolines	2-Aminotetralins (e.g., 8-OH-DPAT) 3,4-DMPEA-NDEPA 5-MeO-N-DEAOP-NET 5-MeO-N-DEAOP-NMT 10,11-Secoergoline (α,N-Pip-T) 10,11-Seco-LSD 25B-NAcPip 25D-NM-NDEAOP (25D-NM-NDEPA) Bay R 1531 (LY-197206) CT-5252 DEIMDHPCA DEMMPDHPCA DEMNDHPCA DEMPDHPCA DEMTMPDHPCA DOB-NDEPA DOI-NDEPA DOM-NDEPA DOTFM-NDEPA LY-178210 LY-293284 M-NDEPA N-DEAOP-NMPEA (PEA-NM-NDEPA) N-DEAOP-NMT NDTDI Phenethylamines RU-27251 RU-27849 RU-28251 RU-28306 TMA-2-NDEPA Tryptamines WXVL_BT0793LQ2118
Related compounds	A-86929 Adrogolide CY-208,243 JRT Naxagolide Quinagolide SDZ SER-082 Voxergolide
Natural sources	Fungi: Clavicipitaceae Claviceps spp. (ergot) Epichloë spp. Periglandula spp. Plants (infected/symbiotic with the above fungi): Achnatherum robustum (sleepy grass) Convolvulaceae (morning glory) Argyreia nervosa (Hawaiian baby woodrose) Ipomoea corymbosa (coaxihuitl, ololiúqui) Ipomoea tricolor (tlitliltzin, badoh negro)
See also: Tryptamines Phenethylamines Psychedelics

1H-LSD

See also

References