82-58-6 Usage
Description
9,10-DIDEHYDRO-6-METHYL-ERGOLINE-8-CARBOXYLIC ACID is a chemical compound that serves as a precursor to the semisynthetic ergot derivatives. However, it does not possess any biological activity on its own. Due to its role as an immediate precursor for the synthesis of LSD, it is subject to controls under the Controlled Substances Act of 1970 in the United States.
Uses
Used in Pharmaceutical Industry:
9,10-DIDEHYDRO-6-METHYL-ERGOLINE-8-CARBOXYLIC ACID is used as a chemical intermediate for the synthesis of various ergot alkaloids and their derivatives, which have significant applications in the pharmaceutical industry. These alkaloids and their derivatives are known for their potent biological activities and are used in the development of drugs for treating various medical conditions.
Used as a Controlled Substance:
9,10-DIDEHYDRO-6-METHYL-ERGOLINE-8-CARBOXYLIC ACID is classified as a controlled substance due to its potential use in the illicit production of LSD, a potent hallucinogen and non-selective serotonin receptor agonist. The regulation and control of this compound aim to prevent its misuse and ensure that it is only used for legitimate scientific and medical purposes.
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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Total synthesis of lysergic acid
Umezaki, Satoshi,Yokoshima, Satoshi,Fukuyama, Tohru
supporting information, p. 4230 - 4233 (2013/09/12)
A total synthesis of lysergic acid was accomplished. Key features of our synthesis include stereoselective construction of the stereogenic centers at the allylic positions by using the Evans aldol reaction, and a sequential process with a ring-closing metathesis and an intramolecular Heck reaction to construct the C and D rings.
Xn:Harmful;
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