Norgestrel

Description

Norgestrel · CAS 6533-00-2 · C21H28O2. UNII HMS5079J18. Melting Point: 205-207 °C.

Identification

CAS Registry Number	6533-00-2
PubChem CID	4542
Molecular formula	C21H28O2
IUPAC name	13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
UNII (FDA)	HMS5079J18

Computed Descriptors

Molecular Weight	312.4
XLogP3	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	312.208930132
Monoisotopic Mass	312.208930132
Topological Polar Surface Area	37.3
Heavy Atom Count	23
Formal Charge	0

Physical & Chemical Properties

Melting Point	205-207 °C

Physical description & handling notes

• Crystals from methanol
• Crystals from diethyl ether-hexane
• In water, 1.73 mg/L, temp not stated.
• Crystals, mp 238-232 °C. Specific optical rotation: +40.7 deg at 25 °C/D (CHCl3) /Norgetrel (+)-form/
• When heated to decomposition, it emits acrid smoke and irritating fumes.
• Mixture of levonorgestrel with ethinyl estradiol. Levlen, Logynon, Microgynon, Nordette, Ovran, Ovranette, Tetre-gynon, Tri-Levlen, Trinordiol, Triphasil. Clinical trial in acne treatment.

GHS Hazard Classification

Reported hazard statements	H315 (11.1%), H319 (11.1%), H351 (92.6%), H360 (88.9%), H362 (88.9%), H400 (88.9%), H410 (88.9%)

Documented Uses

• In a representative chemical synthesis, 6-methoxy-alpha-tetralone is reacted with vinylmagnesium bromide, and the resulting 1,2,3,4-tetrahydro-6-methoxy-1-vinyl-1-naphthol is condensed with 2-ethyl-1,3-cyclopentanedione to form initially a tricyclic intermediate (secosteroid) containing all of the gonane skeleton carbon atoms. Cyclization of the secosteroid via dehydration yields a 13-ethylgona-1,3,5(10)-8,14-pentaene structure which is then successively reduced and ethynylated.
• Prepn: H. Smith, Belg. pat. 623,844 (1963), C.A. 61, 4427c (1964); G.A. Hughes, H. Smith, U.S. pat. 3,959,322 (1976 to Herchel Smith)
• A synthetic steroid hormone used as an ingredient of oral contraceptives
• Norgestrel in combination with ethinyl estradiol is indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception.
• Contraceptives, Oral, Synthetic; Progestational Hormones, Synthetic
• Low-ogestrel (norgestrel and ethinyl estradiol tablets) is indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception. /Included in US product label/

Synonyms

norgestrel; Methylnorethindrone; Ld norgestrel; Norgestrelum; Monovar; Neogest; 6533-00-2; 17-ethynyl-17-hydroxy-18a-homoestr-4-en-3-one; Wy 3707; FH 122-A; SH 850; SH 70850; (-)-NORGESTREL 98; .alpha.-Norgestrel; (.+/-.)-Norgestrel; 13beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one

Frequently Asked Questions

What are the CAS number and molecular formula of Norgestrel?

CAS 6533-00-2; molecular formula C21H28O2; molecular weight — g/mol.

What other names is Norgestrel known by?

norgestrel, Methylnorethindrone, Ld norgestrel, Norgestrelum, Monovar, Neogest.

Is Norgestrel classified as hazardous?

Hazard statements reported: H315, H319, H351, H360, H362.

What are the key physical properties of Norgestrel?

Melting Point: 205-207 °C.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.