Chemistry:ETFELA

ETFELA
Clinical data
Other names	LA-CH2CF3
Identifiers
	IUPAC name (6aR,9R)-N-Ethyl-7-methyl-N-(2,2,2-trifluoroethyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
Chemical and physical data
Formula	C20H22F3N3O
Molar mass	377.411 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC(F)(F)F;
	InChI InChI=1S/C20H22F3N3O/c1-3-26(11-20(21,22)23)19(27)13-7-15-14-5-4-6-16-18(14)12(9-24-16)8-17(15)25(2)10-13/h4-7,9,13,17,24H,3,8,10-11H2,1-2H3/t13-,17-/m1/s1; Key:VAHPXTJQSWECIC-CXAGYDPISA-N;

Short description: Chemical compound

ETFELA (N-ethyl-N-(2,2,2-trifluoroethyl)lysergamide) is an analog of lysergic acid diethylamide (LSD) first synthesised by Jason C. Parrish as part of the research team led by David E. Nichols. In studies in vitro, it was found to be slightly more potent than LSD itself.^[1]^[2]

References

↑ Nichols, David E. (2012). "Structure-activity relationships of serotonin 5-HT_2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. doi:10.1002/wmts.42.
↑ "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences 36: 1–43. 2017. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.

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[1] Nichols, David E. (2012). "Structure-activity relationships of serotonin 5-HT_2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. doi:10.1002/wmts.42.

[2] "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences 36: 1–43. 2017. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.

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[2]

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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Clinical data

Other names	LA-CH₂CF₃
Identifiers
IUPAC name (6aR,9R)-N-Ethyl-7-methyl-N-(2,2,2-trifluoroethyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Chemical and physical data
Formula	C₂₀H₂₂F₃N₃O
Molar mass	377.411 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC(F)(F)F
InChI InChI=1S/C20H22F3N3O/c1-3-26(11-20(21,22)23)19(27)13-7-15-14-5-4-6-16-18(14)12(9-24-16)8-17(15)25(2)10-13/h4-7,9,13,17,24H,3,8,10-11H2,1-2H3/t13-,17-/m1/s1 Key:VAHPXTJQSWECIC-CXAGYDPISA-N

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