Basic information
- CAS
114949-22-3- Standard SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2OC(=O)CCc1ccccc1- InChIKey
UBWXUGDQUBIEIZ-QNTYDACNSA-N- Molecular formula
- C27H34O3
- Average molar mass
- 406.6 g/mol
- Monoisotopic mass
- 406.25079495
Overview
Nandrolone phenpropionate is a 3-phenylpropionate ester. It has a role as an anabolic agent and an androgen. It is functionally related to a nandrolone.
Names & identifiers
- Preferred name
- Nandrolone Phenylpropionate
- IUPAC
- [(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] 3-phenylpropanoate
- English name
- Nandrolone phenylpropionate
- Molecular formula
- C27H34O3
- Molecular weight
- 406.57
Names & synonyms
Show more names
Database identifiers
- CAS
114949-22-3、62-90-8- PubChem CID
- 229455
- DTXSID
DTXSID2023353- ChEMBL
CHEMBL1200412- ChEBI
CHEBI:7468- UNII
- KF7Z9K2T3W
- EC Number
- 200-551-9
- Nikkaji
- J8.621E
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 703
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Physicochemical properties
- Melting point
- 85 · 85-87°C
- Boiling point
- 487.61 °C · 487.61°C (rough estimate)
- alpha
- 58 ° · D +58° (chloroform)
- Density
- 1.014 · 1.0140 (rough estimate)
- refractive index
- 1.546 · 1.5460 (estimate)
- storage temp.
- -20 °C · Controlled Substance, -20°C Freezer
- solubility
- 100 mg/mL · DMSO : 100 mg/mL (245.97 mM; Need ultrasonic)
- form
- Solid
- color
- White to Off-White
- InChIKey
- UBWXUGDQUBIEIZ-QNTYDACNSA-N
- SMILES
- C[C@]12CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]3([H])[C@]1([H])CC[C@@H]2OC(=O)CCC1C=CC=CC=1 |&1:1,4,6,16,18,22,r|
- CAS DataBase Reference
- 62 · 62-90-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 Z9K2T3W · KF7Z9K2T3W
- NCI Drug Dictionary
- ActiVin
- NIST Chemistry Reference
- 4 · 4-Androstene-17-beta-ol-3-one, 19-nor-delta-, phenylpropionate(62-90-8)
- UNSPSC Code
- 12352211 · 12352211
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 351 · H351-H360FD
- Precautionary statements
- 201 · P201-P308+P313
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22-40
- Safety Statements
- 23 · 23-36
- WGK Germany
- 3 · WGK 3
- RTECS
- 7995000 · KG7995000
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 2 Repr · Carc. 2Repr. 1B
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: > 1gm/kg
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (98.2%): 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 57 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Nandrolone phenpropionate
vMost-DILI-concern
7
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- WGK 3
- rtecs
- KG7995000
- Toxicity
- LD50 intraperitoneal in mouse: > 1gm/kg
- risk_code
- 20/21/22-40
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 23-36
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H351-H360FD
- Hazard Classifications
- Carc. 2Repr. 1B
- Precautionary statements
- P201-P308+P313
Chemistry & industry
Pharmacology
Pharmacodynamics
Nandrolone is an anabolic steroid occurring naturally in the human body, albeit in small quantities. Nandrolone increases production and urinary excretion of erythropoietin. It may also have a direct action on bone marrow. Nandrolone binds to the androgen receptor to a greater degree than testosterone, but due to its inability to act on the muscle in ways unmediated by the receptor, has less overall effect on muscle growth.
Mechanism of Action
Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
Absorption, Distribution and Excretion
The absorption after oral dosing is rapid for testosterone and probably for other anabolic steroids, but there is extensive first-pass hepatic metabolism for all anabolic steroids except those that are substituted at the 17-alpha position. The rate of absorption from subcutaneous or intramuscular depots depends on the product and its formulation. Absorption is slow for the lipid-soluble esters such as the cypionate or enanthate, and for oily suspensions.
Uses & manufacturing
Applications
UsesAnabolic steroid; androgen.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
DefinitionChEBI: Nandrolone phenpropionate is a 3-phenylpropionate ester. It has a role as an anabolic agent and an androgen. It is functionally related to a nandrolone.
Related reactions
No reaction records under the current filter.
Compound notes
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