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.
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.
Pharmacologyedit
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]
LSH side effects include sedation, nausea, stimulation, hallucinations (similar to LSD), and euphoria. The headspace is described by many as feeling drunk.
Legalityedit
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 breaks down into LSA which is a Schedule 3 drug and therefore not applicable to the Federal Analog Act
^"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.
^ abHofmann A (1971). "Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico". Bulletin on Narcotics. 1: 3–14.
External linksedit
Ergot - A Rich Source of Pharmacologically Active Substances by Albert Hofmann
May 11, 2024
lysergic, acid, hydroxyethylamide, lysergic, acid, hydroxyethylamide, also, known, lysergic, acid, methyl, carbinolamide, lysergamide, alkaloid, ergoline, family, present, higher, concentrations, parasitic, fungi, species, claviceps, mainly, claviceps, paspali. D Lysergic acid a 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 Lysergic acid hydroxyethylamideClinical dataOther namesD lysergic acid methyl carbinolamideLegal statusLegal statusIllegal in France 1 IdentifiersIUPAC name 9 10 Didehydro N 1 hydroxyethyl 6 methylergoline 8 carboxamideCAS Number3343 15 5 YPubChem CID134553ChemSpider27470958 NCompTox Dashboard EPA DTXSID10955057ECHA InfoCard100 020 079Chemical and physical dataFormulaC 18H 21N 3O 2Molar mass311 385 g mol 13D model JSmol Interactive imageSMILES C C H NC O C H 1CN C H 2Cc3c nH c4c3c ccc4 C2 C1 C OInChI 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 NKey WYTJZJPVCDWOOI KANYHAFZSA N N N Y what is this verify Contents 1 Chemistry 2 Pharmacology 3 Effects 4 Legality 5 See also 6 References 7 External linksChemistry editThe structure is similar to LSD with the N N diethylamide group replaced by an N 1 hydroxyethyl amide in D lysergic acid a hydroxyethylamide Pharmacology editLSH 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 1mg 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 100mg 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 editOne 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 a 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 editD lysergic acid a 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 breaks down into LSA which is a Schedule 3 drug and therefore not applicable to the Federal Analog ActSee also editErgoline Lysergic acid LSA LSD Ergot Hawaiian baby woodrose Argyreia nervosa Ololiuhqui Rivea corymbosa Tlitliltzin Ipomoea violacea verification needed citation needed References edit Arrete du 20 mai 2021 modifiant l arrete du 22 fevrier 1990 fixant la liste des substances classees comme stupefiants www legifrance gouv fr in French 20 May 2021 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 a b Hofmann A 1971 Teonanacatl and Ololiuqui two ancient magic drugs of Mexico Bulletin on Narcotics 1 3 14 External links editErgot A Rich Source of Pharmacologically Active Substances by Albert Hofmann Retrieved from https en wikipedia org w index php title Lysergic acid hydroxyethylamide amp oldid 1214527900, wikipedia, wiki, book, books, library,
