82-58-6 Usage
Description
A precursor of the semisynthetic ergot
derivatives, but having no biological activity itself. It is subject
to controls under the Controlled Substances Act of 1970 in the
United States, since it is the immediate precursor for the synthesis
of LSD. Lysergic acid is obtained by hydrolysis of ergot
alkaloids, either obtained from grains infected with Claviceps
or, more commonly, by fermentation in submerged culture.
Uses
Different sources of media describe the Uses of 82-58-6 differently. You can refer to the following data:
1. Labelled Lysergic acid. Lysergic acid and iso-lysergic acid are the main cleavage products formed on alkaline hydrolysis of the alkaloids which are characteristic of ergot. Potent hallucinogen; non-selective serotonin receptor agonist.
Controlled substanc
2. Lysergic acid and iso-lysergic acid are the main cleavage products formed on alkaline hydrolysis of the alkaloids which are characteristic of ergot. Potent hallucinogen; non-selective serotonin receptor agonist.
Controlled substance.
Definition
ChEBI: An ergoline alkaloid comprising 6-methylergoline having additional unsaturation at the 9,10-position and a carboxy group at the 8-position.
Synthesis Reference(s)
Journal of the American Chemical Society, 78, p. 3087, 1956 DOI: 10.1021/ja01594a039
Flammability and Explosibility
Notclassified
Purification Methods
It crystallises from water as a hydrate. The methyl ester crystallises from C6H6 and has m 168o; the amide [478-94-4] has m 242o(dec) (from MeOH) and []546 +15o (c 0.5, pyridine).The (-)-hydrochloride has m 208-210o(dec, from MeOH). [Kornfeld et al. J Am Chem Soc 7 6 5256 1954,Kornfeld et al. J Am Chem Soc 78 3087 1956, Beilstein 25 III/IV 934,]
Check Digit Verification of cas no
The CAS Registry Mumber 82-58-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 2 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 82-58:
(4*8)+(3*2)+(2*5)+(1*8)=56
56 % 10 = 6
So 82-58-6 is a valid CAS Registry Number.
InChI:InChI=1/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10?,14-/m1/s1
82-58-6Relevant articles and documents
Total synthesis of (+)-lysergic acid
Liu, Qiang,Jia, Yanxing
, p. 4810 - 4813 (2011)
A stereocontrolled total synthesis of (+)-lysergic acid (1) is achieved using three metal-catalyzed methodologies for the construction of three key rings. Highlights of the synthesis include Pd-catalyzed indole synthesis to form the B ring, a RCM reaction to form the D ring, and an intramolecular Heck reaction to form the C ring.
Total synthesis of (+)-lysergic acid
Kanno, Rentaro,Yokoshima, Satoshi,Kanai, Motomu,Fukuyama, Tohru
, p. 240 - 247 (2018)
A total synthesis of (+)-lysergic acid, which features the C-C bond formation between C10 and C11 via cleavage of an aziridine ring, was accomplished.
Total Synthesis of (+/-)-Lysergic Acid by an Intramolecular Imino-Diels-Alder Reaction
Oppolzer, Wolfgang,Francotte, Eric,Baettig, Kurt
, p. 478 - 481 (1981)
(+/-)-Lysergic acid (1) has been synthesized from 4-hydroxymethyl-1-tosylindole (2) by a sequence of 9 steps.The crucial thermolysis 9 ---> 10 involves the in situ-generation of the transient diene III which undergoes an intramolecular cycloaddition to a C,N-double bond at 200 deg C and at low stationary concentration of III.
Erratum: Total synthesis of lysergic acid (Org. Lett. (2013) 15: 16 (4230-4233) DOI: 10.1021/ol4019562)
Umezaki, Satoshi,Yokoshima, Satoshi,Fukuyama, Tohru
supporting information, p. 1269 - 1269 (2014/03/21)
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Xn:Harmful;
This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.