(8alpha,9beta,10alpha,13alpha,14beta)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
Basic information
- CAS
797-64-8- Standard SMILES
C#C[C@@]1(O)CC[C@@H]2[C@H]3CCC4=CC(=O)CC[C@H]4[C@@H]3CC[C@]21CC- InChIKey
WWYNJERNGUHSAO-XHCJJCCMSA-N- Molecular formula
- C21H28O2
- Average molar mass
- 312.4 g/mol
- Monoisotopic mass
- 312.20893013
Overview
Dextronorgestrel is the (+)-enantiomer of norgestrel. It is a 17-ethynyl-17-hydroxy-18a-homoestr-4-en-3-one and a 17alpha-hydroxy steroid. It is an enantiomer of a levonorgestrel.
Names & identifiers
- Preferred name
- (8alpha,9beta,10alpha,13alpha,14beta)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
- IUPAC
- (8S,9R,10S,13R,14R,17S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
- English name
- (-)-NORGESTREL 98
- Molecular formula
- C21H28O2
- Molecular weight
- 312.45
Names & synonyms
Dextronorgestrel797-64-8Z2QG2679YTDTXSID90892173Norgestrel (+)-RefChem:585905DTXCID501079287(8ALPHA,9BETA,10ALPHA,13ALPHA,14BETA)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-EN-20-YN-3-ONE18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (8alpha,9beta,10alpha,13alpha,14beta)-(+)-NorgestrelNorgestrel (+)-formdexonorgestrel
Show more names
l-norgestre1extronorgestrel(-)-NORGESTREL 98(-)-NORGESTREL 98(-)-NORGESTREL 98%13-alpha,14-beta)-h(+) Norgestrel,(+)Norgestrel
L(+)-Norgestrel(8S,9R,10S,13R,14R,17S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one(8S,9R,10S,13R,14R,17S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one(8alpha,9beta,10alpha,13alpha,14beta)-17alpha-ethynyl-17beta-hydroxy-18a-homoestr-4-en-3-one(-)-NORGESTREL 98UNII-Z2QG2679YT1-NORGESTRELLevonorgestrel Impurity 9
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 609
Experimental & physicochemical properties
Human DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 239 · 239-241 °C(lit.)
- alpha
- 25 · D25 +40.7° (CHCl3)
- Boiling point
- 392.36 °C · 392.36°C (rough estimate)
- Density
- 1.0697 · 1.0697 (rough estimate)
- refractive index
- 1.49 · 1.4900 (estimate)
- pka
- 13.09 · 13.09±0.40(Predicted)
- color
- 3 · Crystals from MeOH/CHCl3
- FDA UNII
- 2 QG2679YT · Z2QG2679YT
- EPA Substance Registry System
- 18 · 18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-,(8.alpha.,9.beta.,10.alpha.,13.alpha.,14.beta.)- (797-64-8)
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H332-H360-H312-H351
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 17 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- JF8259000
- Toxicity
- LDLo ipr-mus: 2 g/kg EXCEDS 81,175,83
- risk_code
- 20/21/22-40
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 22-36
- Hazard statements
- H302-H332-H360-H312-H351
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P201-P202-P281-P308+P313-P405-P501-P261-P271-P304+P340-P312
Chemistry & industry
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesL(+)-Norgestrel is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.
Additional notes
DefinitionChEBI: Dexonorgestrel is a 17alpha-hydroxy steroid and a terminal acetylenic compound. It is functionally related to a norgestrel. It is an enantiomer of a levonorgestrel.
Related reactions
0 records
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Compound notes
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