Basic information
- CAS
4097-22-7- Standard SMILES
Nc1ncnc2c1ncn2[C@H]1CC[C@@H](CO)O1- InChIKey
WVXRAFOPTSTNLL-NKWVEPMBSA-N- Molecular formula
- C10H13N5O2
- Average molar mass
- 235.24 g/mol
- Monoisotopic mass
- 235.10692467
Names & identifiers
- Preferred name
- Dideoxyadenosine
- IUPAC
- [(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol
- English name
- Dideoxyadenosine
- Molecular formula
- C10H13N5O2
- Molecular weight
- 235.24
Names & synonyms
Show more names
Database identifiers
- CAS
4097-22-7- PubChem CID
- 20039
- DTXSID
DTXSID2023771- ChEMBL
CHEMBL14925、CHEMBL23094- ChEBI
CHEBI:91207- UNII
- 4Q86AH641A
- EC Number
- 223-853-2
- Nikkaji
- J80.745A
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 99.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 279
Experimental & physicochemical properties
Solubility
10 to 50 mg/mL at 68 °F (NTP, 1992)
H2O 3.4-5.1 (mg/mL)
Buffer, pH4 4.8-9.6 (mg/mL)
Buffer, pH9 3.2-4.8 (mg/mL)
EtOH 1.6-2.0 (mg/mL)
DMA 2.6-3.4 (mg/mL)
Physicochemical properties
- Melting point
- 181 · 181-184 °C(lit.)
- alpha
- 25 · D25 -25.2° (c = 1.01 in water)
- Boiling point
- 377.64 °C · 377.64°C (rough estimate)
- Density
- 1.2455 · 1.2455 (rough estimate)
- refractive index
- -34 ° · -34 ° (C=1, H2O)
- storage temp.
- -20 °C · -20°C
- solubility
- 1 mg/mL; · DMF: 1 mg/mL; DMSO: 2 mg/mL; Ethanol: Slightly soluble
- pka
- 3.84 · pKa 3.84(H2O t=25.0±0. I=0.01) (Uncertain)
- form
- Powder
- color
- White to Off-white
- optical activity
- -28 · [α]/D -28.0±1.0
- Water Solubility
- 43.2 g/L · 43.2g/L(25 ºC)
- Merck
- 14 · 14,3101
- BRN
- 619924 · 619924
- InChI
- 1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1
- InChIKey
- WVXRAFOPTSTNLL-NKWVEPMBSA-N
- SMILES
- Nc1ncnc2n(cnc12)[C@H]3CC[C@@H](CO)O3
- CAS DataBase Reference
- 4097 · 4097-22-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 Q86AH641A · 4Q86AH641A
- NCI Drug Dictionary
- dideoxyadenosine
- EPA Substance Registry System
- 2 · Adenosine, 2',3'-dideoxy- (4097-22-7)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 51 · NA.51
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 341 · H341-H303
- Precautionary statements
- 201 · P201-P202-P280-P308+P313-P405-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- C
- Risk Statements
- 34 · 34-36/37-22
- Safety Statements
- 26 · 26-27-36/37/39-45-24/25
- WGK Germany
- 2 · 2
- RTECS
- 7358900 · AU7358900
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 oral · LD50 oral in mouse: 5gm/kg
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H341 (50%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a freezer. (NTP, 1992)
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Toxicity Data
Mouse(po): LD50: 5 gm/kg
Mouse(sc): LD50: 1320 mg/kg
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- AU7358900
- hs_code
- 29349990
- Toxicity
- LD50 oral in mouse: 5gm/kg
- risk_code
- 34-36/37-22
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- C
- safety_code
- 26-27-36/37/39-45-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H341-H303
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Applications
UsesDideoxy Adenosine (Didanosine EP Impurity G) is a potent anti-HIV agent.
Uses2′,3′-Dideoxyadenosine (ddA), a specific adenylyl cyclase inhibitor, is useful in biological process and pathway studies involving adenylyl cyclase activity and cAMP pool modulation.
UsesA potent labelled anti-HIV agent.
UsesA potent anti-HIV agent.
General DescriptionOff-white powder.
Suppliers100 total
Additional notes
DefinitionChEBI: A purine 2',3'-dideoxyribonucleoside in which the nucleobase component is specified as adenine.
Related reactions
Compound notes
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