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Lysergic acid hydroxyethylamide

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Lysergic acid hydroxyethylamide
Clinical data
Other namesD-lysergic acid methyl carbinolamide
Legal status
Legal status
  • Illegal in France[1]
Identifiers
  • 9,10-Didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.020.079 Edit this at Wikidata
Chemical and physical data
FormulaC18H21N3O2
Molar mass311.385 g·mol−1
3D model (JSmol)
  • C[C@@H](NC(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C)O
  • 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
 ☒NcheckY (what is this?)  (verify)

D-Lysergic acid α-hydroxyethylamide (LSH, LAH), also known as D-lysergic acid methyl carbinolamide, is a Lysergamide and alkaloid of the Ergoline family, it is present in higher concentrations in the parasitic fungi species "Claviceps", mainly the Claviceps paspali, also in Claviceps Purpurea. This fungi grows in various species in the Convolvulaceae family like the Ipomoea violacea (Heavenly Blue Morning Glory), the Rivea corymbosa (Ololiuhqui), and the Argyreia nervosa (Hawaiian Baby Woodrose). Heavenly Blue Morning Glory and Hawaiian Baby Woodrose especially contain high amounts of LSH, with content varying between species and by how fresh the seeds are. LSH is a psychoactive Ergoline and has effects similar to LSD due to similarity in the structure and is the main psychoactive compound found in Claviceps Paspali and in (fresh) Heavenly Blue Morning Glory Seeds. LSH is unstable and breaks down into LSA quickly, so old seeds often only contains LSA and iso-LSA. When the seeds are fresh, they contain significantly higher amounts of LSH.

Chemistry

The structure is similar to LSD, with the N,N- diethylamide group replaced by an N- (1- hydroxyethyl)amide in D-lysergic acid α-hydroxyethylamide.

Pharmacology

LSH has an affinity for several dopamine and serotonin receptors, mainly the 5-HT2 receptor like most psychedelics in the human brain. LSD is a partial agonist on many dopamine and serotonin receptors, so it is highly likely that LSH is also an agonist at dopamine and serotonin receptors.

The intravenous LD50 of the new alkaloid was approximately 150mg/kg for mice and 0.75 mg/kg for rabbits/ Before death, the mice showed periodic convulsions of a clonic type, erection of the hairs and excitability. At doses of 50-100mg/kg it produced only this peculiar symptomatology: the mice stood upright and pressed on each other's noses and chattered their teeth. In rabbits, and injection into the ear vein in doses of 0.1-1mg/kg produced dilatation of the pupil, excitability or convulsions of a clinic type. The ears became pale and cold with intense vasoconstriction. The toxicity of the alkaloid to rabbits seemed to depend on its power of raising the body-temperature in this species. In rabbits the similarity between the effects of the new alkaloid and ergometrine were particularly striking, but ergometrine was less toxic to rabbits (the approximate intravenous LD50 of ergometrine was 3.5mg/kg).

D-lysergic acid methyl carbinolamide induced, in low concentrations (minimum active concentration 0.1-1μg/ml), a contracture in the isolated uterus of the virgen guinea pig. There was a satisfactory dose–response relationship. This contracture was very similar to that produced by ergometrine maleate, which, however, was 1-2 times more potent. On the rabbit uterus in situ both alkaloids produced a prompt contraction and increased rhythmic activity of the uterus. For ergometrine the minimum active dose by intravenous route was 0.1-0.3 mg/kg and for the new alkaloid 0.2-0.5mg/kgm. The actions of both alkaloids lasted some minutes, and owing to the favourable circumstance that the interference between the effects of the two alkaloids was negligible, it was possible to test them on the same preparation. Ergometrine was 1-2 times more potent than the new alkaloid.

On the isolated seminal vesicles of the guinea pig, the new alkaloid was approximately 200 times less potent than ergotamine tartrate as an adrenergic blocking drug. Rabbits anaethetized with urethane supported doses of D-lysergic acid methyl carbinolamide which would have killed unanaesthetized animals. Rapid intravenous injections of small doses (0.1-0.2mg/kg) of the new alkaloid caused an evanescent decrease or a small increase of blood pressure; with higher doses (0.3/0.5mg/kg and more) the blood pressure increased moderately without showing any dose/response relationship.

Ergometrine maleate seemed to be less active on blood pressure, and there was no significant change of blood pressure with 0.3-0.5 mg/kg. The new alkaloid was without effect, when given in small doses, on the blood pressure of cats anaethetized with chloralose. Higher intravenous doses (0.1-0.3mg/kg) caused a sustained hypotension of long duration and a moderate decrease of heart-rate. The respiration of rabbits and cats was depressed by small doses of the new alkaloid; cats seemed to be less resistant than rabbits. In cats, 0.01mg/kg of the new alkaloid caused broncho-constriction and contractions of the nictitating membrane of long duration. The new alkaloid have no action on isolated rabbit auricles at doses up to 100μg/ml.

In summing up, the new naturally occurring alkaloid D-lysergic acid methyl carbinolamide has powerful ergometrine-like oxytocic action and weak ergotamine-like adrenergic blocking actions. It must be included, on the basis of pharmacological evidence, in the ergometrine group of ergot alkaloids. Ergometrine, however, is less toxic and more active than the new alkaloid. Results suggest that it could have a lysergic acid diethylamide-like activity, but this hypothesis must be checked by experiments on humans.[2]

— Glasser, A.

Effects

One of the alkaloids in the seeds of Rivea corymbosa (Ololiuhqui), Argyreia nervosa (Hawaiian Baby Woodrose), and Ipomoea violacea (Tlitliltzin) are ergine (LSA) and isoergine (its epimer).[3]D-lysergic acid α-hydroxyethylamide is very limited/undocumented in human studies.[3]

LSH side effects include sedation, nausea, stimulation, hallucinations (similar to LSD), and euphoria. The headspace is described by many as feeling drunk.

Legality

D-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

References

  1. ^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
  2. ^ Glasser A (January 1961). "Some pharmacological actions of D-lysergic acid methyl carbinolamide". Nature. 189 (4761): 313–4. Bibcode:1961Natur.189..313G. doi:10.1038/189313a0. PMID 13705953. S2CID 4260358.
  3. ^ a b Hofmann A (1971). "Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico". Bulletin on Narcotics. 1: 3–14.
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