Synonym
Anacrotine; Crotalaburnine; NSC 114571; NSC-114571; NSC114571;
IUPAC/Chemical Name
(5R,6R,9a1R,14R,14aS,Z)-3-ethylidene-6,14-dihydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
InChi Key
NPYPUYCITBTPSF-TZCAYXSXSA-N
InChi Code
InChI=1S/C18H25NO6/c1-4-11-7-10(2)18(3,23)17(22)24-9-12-5-6-19-8-13(20)15(14(12)19)25-16(11)21/h4-5,10,13-15,20,23H,6-9H2,1-3H3/b11-4-/t10-,13-,14-,15-,18-/m1/s1
SMILES Code
C/C=C1C[C@H]([C@@](O)(C(OCC2=CCN3C[C@H]([C@H]([C@@H]23)OC/1=O)O)=O)C)C
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
351.40
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 |
1: Hung TC, Lee WY, Chen KB, Chan YC, Chen CY. Insight into HIV of IFN-induced myxovirus resistance 2 (MX2) expressed by traditional Chinese medicine. Biomed Res Int. 2014;2014:871576. doi: 10.1155/2014/871576. Epub 2014 Jun 18. PMID: 25045710; PMCID: PMC4086518.
2: Zündorf I, Wiedenfeld H, Röder E, Dingermann T. Generation and characterization of monoclonal antibodies against the pyrrolizidine alkaloid retrorsine. Planta Med. 1998 Apr;64(3):259-63. doi: 10.1055/s-2006-957421. PMID: 9581524.
3: Mattocks AR, Jukes R. Detection of sulphur-conjugated pyrrolic metabolites in blood and fresh or fixed liver tissue from rats given a variety of toxic pyrrolizidine alkaloids. Toxicol Lett. 1992 Oct;63(1):47-55. doi: 10.1016/0378-4274(92)90106-t. PMID: 1412522.
4: Mattocks AR, Jukes R. Chemistry of sulphur-bound pyrrolic metabolites in the blood of rats given different types of pyrrolizidine alkaloid. Nat Toxins. 1992;1(2):89-95. doi: 10.1002/nt.2620010206. PMID: 1344913.
5: Mattocks AR, Jukes R. Trapping and measurement of short-lived alkylating agents in a recirculating flow system. Chem Biol Interact. 1990;76(1):19-30. doi: 10.1016/0009-2797(90)90031-h. PMID: 2393942.
6: Mattocks AR, Driver HE. Metabolism and toxicity of anacrotine, a pyrrolizidine alkaloid, in rats. Chem Biol Interact. 1987;63(1):91-104. doi: 10.1016/0009-2797(87)90107-4. PMID: 3652286.
7: Sinsheimer JE, Van den Eeckhout E, Hooberman BH, Beylin VG. Detoxication of aliphatic epoxides by diol formation and glutathione conjugation. Chem Biol Interact. 1987;63(1):75-90. doi: 10.1016/0009-2797(87)90106-2. PMID: 3308149.
8: Culvenor CC, Edgar JA, Jago MV, Qutteridge A, Peterson JE, Smith LW. Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure. Chem Biol Interact. 1976 Mar;12(3-4):299-324. doi: 10.1016/0009-2797(76)90046-6. PMID: 1253333.
9: Ghosh MN, Singh H. Inhibitory effect of a pyrrolizidine alkaloid, crotalaburnine, on rat paw oedema and cotton pellet granuloma. Br J Pharmacol. 1974 Aug;51(4):503-8. doi: 10.1111/j.1476-5381.1974.tb09668.x. PMID: 4451764; PMCID: PMC1778073.