3740 Lysergic acid hydroxyethylamide Lysergic acid hydroxyethylamide (LSH) is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. It is structurally is similar to LSD, with the N,N- diethylamide group replaced by an N- (1- hydroxyethyl)amide in D-lysergic acid α-hydroxyethylamide. It's effect on humans has not been thoroughly studied, but long term exposure to many ergoline alkaloids is known to cause ergotism, a disease causing convulsive and gangrenous symptoms. (L1918, L1926) 3343-15-5 134553 C18H21N3O2 White powder. Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Animal studies of LSH have shown it to have oxytocic and adrenergic blocking effects similar to ergometrine. (A2914, A2915, A2916, A2919) LD50: 150 mg/kg (Intravenous, Mouse) (A2919) No indication of carcinogenicity to humans (not listed by IARC). Lysergic acid hydroxyethylamide (LSH) is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. (L1918) Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913) Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920) Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921) 2010-04-23T14:28:06Z 2014-12-24T20:26:22Z http://en.wikipedia.org/wiki/Lysergic_acid_hydroxyethylamide true CC(O)NC(=O)C1CN(C)C2CC3=CNC4=CC=CC(=C34)C2=C1 C18H21N3O2 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) InChIKey=WYTJZJPVCDWOOI-UHFFFAOYSA-N 311.3782 311.163376931 Exogenous Solid