BU-LAD

BU-LAD
Clinical data
Other names	BU-LAD, 6-butyl-6-nor-Lysergic acid diethylamide
Routes of; administration	Oral
Legal status
Legal status	US: Analogue to a Schedule I/II drug (but only if it is intended for human consumption);
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
	IUPAC name (6aR,9R)-7-butyl-N,N-diethyl-4,6,6a,7,8,9- hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	96930-87-9 ;
PubChem CID	44457782;
ChemSpider	21106266 ;
UNII	4Z2TQQ6ZTC;
ChEMBL	ChEMBL22520 ;
CompTox Dashboard (EPA)	DTXSID901165228 ;
Chemical and physical data
Formula	C23H31N3O
Molar mass	365.521 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)[C@@H]2C=C1c3cccc4[nH]cc(C[C@H]1N(C2)CCCC)c34;
	InChI InChI=1S/C23H31N3O/c1-4-7-11-26-15-17(23(27)25(5-2)6-3)12-19-18-9-8-10-20-22(18)16(14-24-20)13-21(19)26/h8-10,12,14,17,21,24H,4-7,11,13,15H2,1-3H3/t17-,21-/m1/s1 ; Key:VTVHSIXDKKKTMT-DYESRHJHSA-N ;
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BU-LAD, also known as 6-butyl-6-nor-lysergic acid diethylamide, is an analogue of LSD first made by Alexander Shulgin and reported in the book TiHKAL. BU-LAD is a psychedelic drug similar to LSD, but is significantly less potent than LSD,^[1] with a dose of 500 micrograms producing only mild effects.

References

^ 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.

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[pmid4032428-1] 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.

[1]

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) 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 Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide 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 Brazergoline Cianergoline CY-208,243 Delergotrile Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
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)