Synonym
Dimercaprol; BAL; Dithioglycerol; DMP; Sulfactin; HSDB4004; HSDB-4004; HSDB 4004; NSC4646; NSC 4646; NSC-4646
IUPAC/Chemical Name
1-Propanol, 2,3-dimercapto-
InChi Key
WQABCVAJNWAXTE-UHFFFAOYSA-N
InChi Code
InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Dimercaprol in anti-gas warfare agent that is effective against Lewisite (dichloro(2-chlorovinyl)arsine) and formerly known as British Anti-Lewisite or BAL.
In vitro activity:
DMP (2,3 dimercapto-1-propanol) inhibited transactivation directed by tat protein, which is a metal containing transcriptional transactivating factor and also interfered with viral production. Furthermore, treatment and pretreatment of cells with DMP strongly reduced their sensitivity for HIV-1 infection through unknown mechanisms. These results indicate that DMP reveals pleuripotent effects on HIV-1 infection and production in vitro and thus may provide an exploitable hypothesis for designing new drugs against AIDS.
Reference: AIDS Res Hum Retroviruses. 1990 Jul;6(7):919-27. https://pubmed.ncbi.nlm.nih.gov/2202353/
In vivo activity:
The maximal time on the rotarod in all the groups (sham injury group, 6-OHDA (6-hydroxydopamine), and 6-OHDA+DP (dimercaprol)) before surgery was 330 s. 6-OHDA injection gradually reduced the maximal time on the rotarod, with a significant reduction starting at week 3 (198 ± 67.7 s) compared to the sham injury group (327 ± 5.8 s). However, systemic treatment with 5 mg/kg DP significantly mitigated the reduction at weeks 4 and 5 (318 ± 23.5 s and 300 ± 40.1 s, respectively), compared to the 6-OHDA group at the corresponding time points (174 ± 65.0 s and 167 ± 24.3 s, respectively) (Fig. 3a).
Reference: Transl Neurodegener. 2021 Apr 28;10(1):13. https://pubmed.ncbi.nlm.nih.gov/33910636/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| Water |
41.7 |
335.46 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
124.22
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Kubota S, el-Farrash MA, Maki M, Harada S, Hatanaka M. 2,3 Dimercapto-1-propanol inhibits HIV-1 tat activity, viral production, and infectivity in vitro. AIDS Res Hum Retroviruses. 1990 Jul;6(7):919-27. doi: 10.1089/aid.1990.6.919. PMID: 2202353.
2. Shi L, Lin Y, Jiao Y, Herr SA, Tang J, Rogers E, Chen Z, Shi R. Acrolein scavenger dimercaprol offers neuroprotection in an animal model of Parkinson's disease: implication of acrolein and TRPA1. Transl Neurodegener. 2021 Apr 28;10(1):13. doi: 10.1186/s40035-021-00239-0. PMID: 33910636; PMCID: PMC8080346.
3. Tian R, Shi R. Dimercaprol is an acrolein scavenger that mitigates acrolein-mediated PC-12 cells toxicity and reduces acrolein in rat following spinal cord injury. J Neurochem. 2017 Jun;141(5):708-720. doi: 10.1111/jnc.14025. Epub 2017 May 3. PMID: 28301040; PMCID: PMC5429218.
In vitro protocol:
1. Kubota S, el-Farrash MA, Maki M, Harada S, Hatanaka M. 2,3 Dimercapto-1-propanol inhibits HIV-1 tat activity, viral production, and infectivity in vitro. AIDS Res Hum Retroviruses. 1990 Jul;6(7):919-27. doi: 10.1089/aid.1990.6.919. PMID: 2202353.
In vivo protocol:
1. Shi L, Lin Y, Jiao Y, Herr SA, Tang J, Rogers E, Chen Z, Shi R. Acrolein scavenger dimercaprol offers neuroprotection in an animal model of Parkinson's disease: implication of acrolein and TRPA1. Transl Neurodegener. 2021 Apr 28;10(1):13. doi: 10.1186/s40035-021-00239-0. PMID: 33910636; PMCID: PMC8080346.
2. Tian R, Shi R. Dimercaprol is an acrolein scavenger that mitigates acrolein-mediated PC-12 cells toxicity and reduces acrolein in rat following spinal cord injury. J Neurochem. 2017 Jun;141(5):708-720. doi: 10.1111/jnc.14025. Epub 2017 May 3. PMID: 28301040; PMCID: PMC5429218.
1: Tian R, Shi R. Dimercaprol is an acrolein scavenger that mitigates acrolein- mediated PC-12 cells toxicity and reduces acrolein in rat following spinal cord injury. J Neurochem. 2017 Jun;141(5):708-720. doi: 10.1111/jnc.14025. Epub 2017 May 3. PMID: 28301040; PMCID: PMC5429218.
2: Mückter H, Liebl B, Reichl FX, Hunder G, Walther U, Fichtl B. Are we ready to replace dimercaprol (BAL) as an arsenic antidote? Hum Exp Toxicol. 1997 Aug;16(8):460-5. doi: 10.1177/096032719701600807. PMID: 9292286.
3: DIMERCAPROL for hepatolenticular degeneration. Lancet. 1952 Jan 26;1(6700):199-200. PMID: 14889814.
4: DIMERCAPROL: BAL. Bull Am Soc Hosp Pharm. 1946 May-Jun;3(3):76. PMID: 20247093.
5: Vilensky JA, Redman K. British anti-Lewisite (dimercaprol): an amazing history. Ann Emerg Med. 2003 Mar;41(3):378-83. doi: 10.1067/mem.2003.72. PMID: 12605205.
6: England JM, Smith DS. Gold-induced thrombocytopenia and response to dimercaprol. Br Med J. 1972 Jun 24;2(5816):748-9. doi: 10.1136/bmj.2.5816.748. PMID: 5036882; PMCID: PMC1788478.
7: MONTUSCHI E. Mercuric chloride poisoning treated with dimercaprol. Br Med J. 1953 Sep 5;2(4835):545. doi: 10.1136/bmj.2.4835.545. PMID: 13082034; PMCID: PMC2029671.
8: KEILLER FE, WARIN RP. Mercury dermatitis in a tattoo: treated with dimercaprol. Br Med J. 1957 Mar 23;1(5020):687. doi: 10.1136/bmj.1.5020.687. PMID: 13404275; PMCID: PMC1974617.
9: Hughes RD, Gazzard BG, Hanid MA, Trewby PN, Murray-Lyon IM, Davis M, Williams R, Bennet JR. Controlled trial of cysteamine and dimercaprol after paracetamol overdose. Br Med J. 1977 Nov 26;2(6099):1395. doi: 10.1136/bmj.2.6099.1395. PMID: 338110; PMCID: PMC1632345.
10: CLAYTON BE, PATRICK AD. Use of dimercaprol or pencillamine in the treatment of cystinosis. Lancet. 1961 Oct 21;2(7208):909-10. PMID: 13879842.
