Diallyllysergamide

Diallyllysergamide
Clinical data
Other names	DAL, Lysergic acid diallylamide, d-lysergic acid diallylamide, d-diallyllysergamide
Routes of; administration	Oral
ATC code	none;
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)-N,N-Diallyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide;
CAS Number	73032-97-0;
PubChem CID	57481013;
ChemSpider	21106294 ;
CompTox Dashboard (EPA)	DTXSID501046535 ;
ECHA InfoCard	100.163.206
Chemical and physical data
Formula	C22H25N3O
Molar mass	347.462 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C=CCN(CC=C)C(=O)[C@@H]2C=C1c3cccc4[nH]cc(C[C@H]1N(C)C2)c34;
	InChI InChI=1S/C22H25N3O/c1-4-9-25(10-5-2)22(26)16-11-18-17-7-6-8-19-21(17)15(13-23-19)12-20(18)24(3)14-16/h4-8,11,13,16,20,23H,1-2,9-10,12,14H2,3H3/t16-,20-/m1/s1 ; Key:VAMQYGHNZLRSSA-OXQOHEQNSA-N ;
	(verify)

N,N-Diallyllysergamide (DAL, as the tartrate salt) is a psychedelic lysergamide.^[1] In their book TiHKAL, Alexander and Ann Shulgin describe it as being "an order of magnitude less potent than LSD itself".

References

^ Nichols DE (2018). Halberstadt AL, Vollenweider FX, Nichols DE (eds.). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36. Springer: 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.

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[pmid28401524-1] Nichols DE (2018). Halberstadt AL, Vollenweider FX, Nichols DE (eds.). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36. Springer: 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.

[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)