Lysergic acid hydroxyethylamide

Lysergic acid hydroxyethylamide (LSH or LAH), also known as lysergic acid N-(α-hydroxyethyl)amide, is an ergoamide and an ergoline. It is perhaps the main constituent of the parasitic fungus, Claviceps paspali;^[2][3][4] and found in trace amounts in Claviceps purpurea.^[5][6] C. paspali and C. purpurea are ergot-spreading fungi. Periglandula, Clavicipitacepus fungi, are permanently symbiotically connected to an estimated 450 species of Convolvulaceae^[7] and thus generate LAH in some of them (42 generate ergolines, by Eckart Eich's review^[8]). The most well-known ones are Ipomoea tricolor (“morning glory”), Turbina corymbosa (coaxihuitl), and Argyreia nervosa (Hawaiian baby woodrose). LAH is structurally similar to ergonovine, which is also known as lysergic acid hydroxymethylethylamide.

LSH

Clinical data
Other names	LAH; LSH; Lysergic acid N-(α-hydroxyethyl)amide; ᴅ-Lysergic acid methyl carbinolamide; N-(1-Hydroxyethyl)lysergamide; N(HOE)-LA; Lysergic acid-α-hydroxyethylamide
Legal status
Legal status	Illegal in France[1]
Identifiers
IUPAC name 9,10-Didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide
CAS Number	3343-15-5 Y
PubChem CID	134553
ChemSpider	27470958 N
CompTox Dashboard (EPA)	DTXSID10955057
ECHA InfoCard	100.020.079
Chemical and physical data
Formula	C18H21N3O2
Molar mass	311.385 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@@H](NC(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C)O
InChI InChI=1S/C18H21N3O2/c1-10(22)20-18(23)12-6-14-13-4-3-5-15-17(13)11(8-19-15)7-16(14)21(2)9-12/h3-6,8,10,12,16,19,22H,7,9H2,1-2H3,(H,20,23)/t10-,12+,16+/m0/s1 N Key:WYTJZJPVCDWOOI-KANYHAFZSA-N N
NY (what is this?)  (verify)

The more well-known analog, lysergic acid amide (syn. ergine), is more prominent in analytical results because LAH easily decomposes to ergine.^[9][10] Ergine is only present because of the decomposition of LAH (and lysergic acid hydroxymethylethylamide and ergopeptines or their ergopeptam precursors); it is not generated.^{[11][12][13][14][15]} Indeed, a 2016 analysis found that fresher I. tricolor seeds contained more LAH than the other two batches analyzed^[16] (another interesting finding is that penniclavine was the predominant ergoline.)

Pharmacology

The pharmacology of LSH has been very limitedly studied.^[9][17][18] It has about 30 to 50% of the potency as ergometrine as an oxytocic in the isolated guinea pig and rabbit uterus, produces sympathomimetic effects (including piloerection, mydriasis, and hyperthermia) very similar to those of ergine in mice and rabbits, and has weak ergotamine-like sympatholytic or antiadrenergic effects (1/200 the potency of ergotamine).^[9][18] These effects are potentially indicative of LSH having LSD-like activity.^[9][17][18] However, LSH is not known to have been tested in humans.^[17][18] LSH may simply function as a prodrug of ergine.^[17][9]

Chemistry

The structure of LSH is similar to that of LSD, with the N,N-diethylamide group replaced by an N-(1-hydroxyethyl)amide in D-lysergic acid α-hydroxyethylamide. LSH is also very similar in structure to ergonovine (ergometrine), which is also known as lysergic acid hydroxyisopropylamide.^[19]

Legal status

ᴅ-lysergic acid α-hydroxyethylamide is unscheduled and uncontrolled in the United States, but possession and sales of it for human consumption could potentially be prosecuted under the Federal Analog Act because of its structural similarities to LSD. Although doubtful as it breaks down into LSA which is a Schedule 3 drug and therefore not applicable to the Federal Analog Act.

See also

• Ergoline
• Lysergic acid
• LSA
• LSD
• Ergot
• Hawaiian baby woodrose (Argyreia nervosa)
• Ololiuhqui (Rivea corymbosa)
• Tlitliltzin (Ipomoea tricolor)