 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C10H5CL7O |
| Molecular Weight | 389.32 |
| Exact Mass | 385.816 |
| CAS # | 1024-57-3 |
| PubChem CID | 13930 |
| Appearance | White to off-white solid powder |
| Density | 1.9±0.1 g/cm3 |
| Boiling Point | 425.5±45.0 °C at 760 mmHg |
| Melting Point | 160-161.5℃ |
| Flash Point | 162.2±28.8 °C |
| Vapour Pressure | 0.0±1.0 mmHg at 25°C |
| Index of Refraction | 1.662 |
| LogP | 5.47 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 18 |
| Complexity | 505 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | [C@H]12[C@H]([C@H]3[C@@H]([C@@H]1Cl)O3)[C@@]4(C(=C([C@]2(C4(Cl)Cl)Cl)Cl)Cl)Cl |
| InChi Key | ZXFXBSWRVIQKOD-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C10H5Cl7O/c11-3-1-2(4-5(3)18-4)9(15)7(13)6(12)8(1,14)10(9,16)17/h1-5H |
| Chemical Name | 1,6,8,9,10,11,11-heptachloro-4-oxatetracyclo[6.2.1.02,7.03,5]undec-9-ene |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion RATS FED 30 MG/KG HEPTACHLOR HAD MAXIMUM CONCN OF HEPTACHLOR EPOXIDE IN FAT WITHIN 2-4 WEEKS; 12 WEEKS AFTER EXPOSURE ... DISCONTINUED, HEPTACHLOR EPOXIDE HAD COMPLETELY DISAPPEARED FROM ADIPOSE TISSUE. The chief route of excretion is biliary, although nearly all organochlorines yield measurable urinary metabolites. ... Many of the unmetabolized pesticides are efficiently reabsorbed by the intestine (enterohepatic ciruclation) substantially retarding fecal excretion. /Solid organochlorine insecticides/ HEPTACHLOR CAN BE ABSORBED THROUGH SKIN & VIA LUNG & GASTROENTERIC TRACT. IN RAT, HEPTACHLOR IS METABOLIZED TO HEPTACHLOR EPOXIDE. HEPTACHLOR EPOXIDE IS ALSO THE OXIDATION PRODUCT OF HEPTACHLOR IN OTHER ANIMALS, AS WELL AS IN PLANTS & MICROORGANISMS, BUT NOT ALL HEPTACHLOR IS CONVERTED TO THE EPOXIDE, WHICH IS MORE TOXIC & MORE STABLE THAN THE PARENT COMPOUND. HEPTACHLOR EPOXIDE IS ... FOUND IN BLOOD & FAT OF STILLBORN INFANTS, INDICATING TRANSPLACENTAL TRANSFER TO THE FETUS. IT IS ALSO EXCRETED IN HUMAN MILK. For more Absorption, Distribution and Excretion (Complete) data for HEPTACHLOR EPOXIDE (11 total), please visit the HSDB record page. Metabolism / Metabolites ... FECAL METABOLITE (A DEHYDROGENATED DERIVATIVE OF 1-HYDROXY-2,3-EPOXYCHLORDENE) WAS ISOLATED FROM RATS FED 10 MG/KG DIET HEPTACHLOR EPOXIDE FOR 30 DAYS. DEHYDROCHLORINATION OF HEPTACHLOR EPOXIDE, FOLLOWED BY HYDROXYLATION & DOUBLE-BOND REARRANGEMENT, LEADS TO FORMATION OF METABOLITE WHICH IS THE PRINCIPAL FORM ... EXCRETED IN FECES. A 3-DAY AQUATIC SYSTEM WAS USED TO EVALUATE UPTAKE & BIOTRANSFORMATION OF HEPTACHLOR EPOXIDE. WATER SAMPLES INDICATED RAPID FORMATION (APPROX 24 HR) OF 1-HYDROXYCHLORDENE & ITS EPOXIDE PLUS A POLAR METABOLITE FROM SNAIL (PHYSA & OEDOGONIUM), MOSQUITO (CULEX) & FISH (GAMBUSIA). GROWING BROTH CULTURES OF NOCARDIOSIS METABOLIZED PURE CIS- OR TRANS-CHLORDANE TO AT LEAST 8 SOLVENT-SOLUBLE SUBSTANCES INCLUDING HEPTACHLOR ENDO-EPOXIDE. For more Metabolism/Metabolites (Complete) data for HEPTACHLOR EPOXIDE (9 total), please visit the HSDB record page. Heptachlor epoxide is readily absorbed by the skin, lungs and gastrointestinal tract and excreted in the urine and faeces. (L118) |
| Toxicity/Toxicokinetics |
Toxicity Summary Heptachlor epoxide is a central nervous system stimulant. It non-competitively blocks neurotransmitter action at gamma-amino butyric acid receptors, resulting in overstimulation of the nervous system. Heptachlor epoxide is also believed to exert carcinogenic effects by activating key kinases in signalling pathways and inhibiting apoptosis. (L118, A81, A82) |
| Additional Infomation |
Heptachlor is a manufactured chemical and doesn't occur naturally. Pure heptachlor is a white powder that smells like camphor (mothballs). The less pure grade is tan. Trade names include Heptagran®, Basaklor®, Drinox®, Soleptax®, Termide®, and Velsicol 104®. Heptachlor was used extensively in the past for killing insects in homes, buildings, and on food crops, especially corn. These uses stopped in 1988. Currently it can only be used for fire ant control in power transformers. Heptachlor epoxide is also a white powder. Bacteria and animals break down heptachlor to form heptachlor epoxide. The epoxide is more likely to be found in the environment than heptachlor. Heptachlor Epoxide can cause cancer according to an independent committee of scientific and health experts. Heptachlor epoxide appears as a degradation product of heptachlor that occurs in soil and in or on crops when treatments with heptachlor, an insecticide, have been made. Forms readily upon exposing heptachlor to air. Heptachlor epoxide is a member of oxanes. Heptachlor epoxide is a chemical produced when heptachlor is broken down by bacteria and animals. Heptachlor is a manufactured cyclodiene organochlorine insecticide. As it is a persistant organic pollutant, heptachlor use is banned or limited in most areas. The epoxide is more likely to be found in the environment than heptachlor. (L118, L119) An oxidation product of HEPTACHLOR formed by many plants and animals, including humans, after exposure to HEPTACHLOR. It has been shown to remain in soil treated with HEPTACHLOR for over fifteen years and is toxic to animals and humans. (From ATSDR Public Heath Statement, April 1989) Mechanism of Action EVIDENCE INDICATES THAT CYCLODIENE-TYPE-INSECTICIDES, EG, HEPTACHLOR EPOXIDE, MIMIC ACTION OF PICROTOXININ. THESE INSECTICIDES INHIBIT THE GAMMA-AMINOBUTYRIC ACID-STIMULATED CHLORIDE UPTAKE IN COXAL MUSCLE OF AMERICAN COCKROACH, & DIRECTLY COMPETE AGAINST LABELED DIHYDROpICROTOXININ FOR BINDING IN THE RAT BRAIN SYNAPTOSOMES. MOREOVER, SEVERAL CYCLODIENE RESISTANT INSECT STRAINS ARE RESISTANT TO PICROTOXININ. THIS CROSS-RESISTANCE IS SPECIFIC TO PICROTOXININ & DOES NOT EXTEND TO OTHER NEUROEXCITANTS. THESE INSECTICIDES, LIKE PICROTOXININ, CAUSE CENTRAL NERVOUS EXCITATION BY STIMULATING TRANSMITTER RELEASE. THESE RESULTS INDICATE THAT SOME OF THE NERVE EXCITATION SYMPTOMS THAT INSECTICIDES CAUSE ARE LIKELY DUE TO THEIR INTERACTION WITH PICROTOXININ RECEPTOR. The actions of the polychlorocycloalkane insecticide heptachlor, and its epoxide metabolite, were examined on GABA receptors in insects and vertebrates. Electrophysiological experiments on the cell body of the cockroach (Periplaneta americana) fast coxal depressor motor neuron, and GABA activated (36)Cl- uptake experiments on microsacs perpared from cockroach ventral nerve cords showed that both heptachlor and heptachlor epoxide blocked functional GABA receptors. The block appeared to be non-competitive and was voltage independent over the membrane potential range -75 mV to -110 mV. There was no significant difference between the potencies of heptachlor and heptachlor epoxide in the functional assays for insect GABA receptors. Both cmpd inhibited (35)S-t-butylbicyclophosphorothionate binding in insects and vertebrates. The findings provide further evidence fo block of an insect GABA receptor/Cl- channel by the cyclodiene class of polychlorocycloalkanes, and reveal differences in the insecticide-(35)S-t-butylbicyclophosphorothionate binding site interactions of insects and vertebrates. Drug Warnings Food and Environmental Agents: Effect on Breast-Feeding: Heptachlorepoxide: None. /from Table 7/ |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5686 mL | 12.8429 mL | 25.6858 mL | |
| 5 mM | 0.5137 mL | 2.5686 mL | 5.1372 mL | |
| 10 mM | 0.2569 mL | 1.2843 mL | 2.5686 mL |