MedKoo Cat#: 464072 | Name: Heptachlor
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Heptachlor is an organochlorine compound that was used as an insecticide. Usually sold as a white or tan powder, heptachlor is one of the cyclodiene insecticides. In 1962, Rachel Carson's Silent Spring questioned the safety of heptachlor and other chlorinated insecticides. Due to its highly stable structure, heptachlor can persist in the environment for decades. In the United States, the Environmental Protection Agency has limited the sale of heptachlor products to the specific application of fire ant control in underground transformers. The amount that can be present in different foods is regulated.

Chemical Structure

Heptachlor
Heptachlor
CAS#76-44-8

Theoretical Analysis

MedKoo Cat#: 464072

Name: Heptachlor

CAS#: 76-44-8

Chemical Formula: C10H5Cl7

Exact Mass: 369.8211

Molecular Weight: 373.30

Elemental Analysis: C, 32.18; H, 1.35; Cl, 66.47

Price and Availability

Size Price Availability Quantity
100mg USD 485.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Heptachlor; Heptachlorane; Heptachlore; Heptachloor; NSC 8930; NSC8930; NSC-8930;
IUPAC/Chemical Name
1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-1H-4,7-methanoindene
InChi Key
FRCCEHPWNOQAEU-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H5Cl7/c11-4-2-1-3-5(4)9(15)7(13)6(12)8(3,14)10(9,16)17/h1-5H
SMILES Code
ClC1C=CC2C1C3(C(Cl)=C(C2(C3(Cl)Cl)Cl)Cl)Cl
Appearance
Solid powder
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
>2 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
More Info
Product Data
Biological target:
Organochlorine compound that was used as an insecticide.
In vitro activity:
In order to evaluate its toxicity towards cell membranes, heptachlor was made to interact with human erythrocytes and molecular models of the red cell membrane. Observations by scanning electron microscopy showed that 10 mM heptachlor produced various degrees of shape alterations to erythrocytes, which ranged from a few blebs in some cells to a great number of protuberances in others. On the other hand, experiments performed by X-ray diffraction on DMPC and DMPE indicated that the bilayer structure of DMPC was much more affected by heptachlor than that of DMPE. Measurements by fluorescence spectroscopy on DMPC LUV confirmed the X-ray diffraction results in that both the hydrocarbon chain and polar head regions of DMPC were structurally perturbed by heptachlor. The results obtained from the model studies could explain the shape changes induced to red cells by heptachlor. According to the bilayer hypothesis, they were due to the preferential interaction of heptachlor with the phosphatidylcholine-rich external moiety of the erythrocyte membrane. It is therefore concluded that toxic effects of this pesticide can be related to its capacity to perturb the phospholipid bilayer structure, whose integrity is essential for cell membrane functions. Reference: Biochim Biophys Acta. 1997 May 22;1326(1):115-23. https://pubmed.ncbi.nlm.nih.gov/9188806/
In vivo activity:
To further examine whether heptachlor induced selective toxicity in the SN leading to apoptotic cell death, activities of caspases were monitored in the different brain areas of the heptachlor-injected mice. The brains from the injected mice were dissected into cerebellum, cortex and SN for the measurement of fluorogenic substrate-cleaving activities for caspase-1, -3 and -9. Figure 2e shows that all three of the substrate-cleaving activities were significantly elevated in the SN tissue lysates, whereas those of cerebellum and cortex remained basal or slightly increased. This result further suggests that heptachlor may have selective toxicity against SN and induced caspase-mediated apoptosis in vivo. Reference: Exp Mol Med. 2014 Feb 28;46(2):e80. https://pubmed.ncbi.nlm.nih.gov/24577234/
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
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 373.30 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.

Recalculate based on batch purity %
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. Suwalsky M, Benites M, Villena F, Aguilar F, Sotomayor CP. The organochlorine pesticide heptachlor disrupts the structure of model and cell membranes. Biochim Biophys Acta. 1997 May 22;1326(1):115-23. doi: 10.1016/s0005-2736(97)00019-9. PMID: 9188806. 2. Hong S, Hwang J, Kim JY, Shin KS, Kang SJ. Heptachlor induced nigral dopaminergic neuronal loss and Parkinsonism-like movement deficits in mice. Exp Mol Med. 2014 Feb 28;46(2):e80. doi: 10.1038/emm.2014.12. PMID: 24577234; PMCID: PMC3944446. 3. Richardson JR, Caudle WM, Wang MZ, Dean ED, Pennell KD, Miller GW. Developmental heptachlor exposure increases susceptibility of dopamine neurons to N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)in a gender-specific manner. Neurotoxicology. 2008 Sep;29(5):855-63. doi: 10.1016/j.neuro.2008.05.007. Epub 2008 Jun 5. PMID: 18577399; PMCID: PMC2574680.
In vitro protocol:
1. Suwalsky M, Benites M, Villena F, Aguilar F, Sotomayor CP. The organochlorine pesticide heptachlor disrupts the structure of model and cell membranes. Biochim Biophys Acta. 1997 May 22;1326(1):115-23. doi: 10.1016/s0005-2736(97)00019-9. PMID: 9188806.
In vivo protocol:
1. Hong S, Hwang J, Kim JY, Shin KS, Kang SJ. Heptachlor induced nigral dopaminergic neuronal loss and Parkinsonism-like movement deficits in mice. Exp Mol Med. 2014 Feb 28;46(2):e80. doi: 10.1038/emm.2014.12. PMID: 24577234; PMCID: PMC3944446. 2. Richardson JR, Caudle WM, Wang MZ, Dean ED, Pennell KD, Miller GW. Developmental heptachlor exposure increases susceptibility of dopamine neurons to N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)in a gender-specific manner. Neurotoxicology. 2008 Sep;29(5):855-63. doi: 10.1016/j.neuro.2008.05.007. Epub 2008 Jun 5. PMID: 18577399; PMCID: PMC2574680.
1: Cao F, Li Z, He Q, Lu S, Qin P, Li L. Occurrence, spatial distribution, source, and ecological risk assessment of organochlorine pesticides in Dongting Lake, China. Environ Sci Pollut Res Int. 2021 Feb 16. doi: 10.1007/s11356-021-12743-x. Epub ahead of print. PMID: 33594570. 2: Buah-Kwofie A, Humphries MS. Organochlorine pesticide accumulation in fish and catchment sediments of Lake St Lucia: Risks for Africa's largest estuary. Chemosphere. 2021 Jan 25;274:129712. doi: 10.1016/j.chemosphere.2021.129712. Epub ahead of print. PMID: 33529950. 3: Park EY, Kim J, Park E, Oh JK, Kim B, Lim MK. Serum concentrations of persistent organic pollutants and colorectal cancer risk: A case-cohort study within Korean National Cancer Center Community (KNCCC) cohort. Chemosphere. 2021 Jan 8;271:129596. doi: 10.1016/j.chemosphere.2021.129596. Epub ahead of print. PMID: 33460900. 4: Dasgupta S, Peng X, Xu H, Ta K, Chen S, Li J, Du M. Deep seafloor plastics as the source and sink of organic pollutants in the northern South China Sea. Sci Total Environ. 2021 Apr 15;765:144228. doi: 10.1016/j.scitotenv.2020.144228. Epub 2020 Dec 24. PMID: 33412380. 5: Sosan MB, Adeleye AO, Oyekunle JAO, Udah O, Oloruntunbi PM, Daramola MO, Saka WT. Dietary risk assessment of organochlorine pesticide residues in maize-based complementary breakfast food products in Nigeria. Heliyon. 2020 Dec 22;6(12):e05803. doi: 10.1016/j.heliyon.2020.e05803. PMID: 33385092; PMCID: PMC7770536. 6: Yang W, Ni W, Jin L, Liu J, Li Z, Wang L, Ren A. Determination of organochlorine pesticides in human umbilical cord and association with orofacial clefts in offspring. Chemosphere. 2021 Mar;266:129188. doi: 10.1016/j.chemosphere.2020.129188. Epub 2020 Dec 3. PMID: 33310357. 7: Mbusnum KG, Malleret L, Deschamps P, Khabouchi I, Asia L, Lebarillier S, Menot G, Onguene R, Doumenq P. Persistent organic pollutants in sediments of the Wouri Estuary Mangrove, Cameroon: Levels, patterns and ecotoxicological significance. Mar Pollut Bull. 2020 Nov;160:111542. doi: 10.1016/j.marpolbul.2020.111542. Epub 2020 Oct 5. PMID: 33181915. 8: Gautam S, Sood NK, Gupta K, Joshi C, Gill KK, Kaur R, Chauhan I. Bioaccumulation of pesticide contaminants in tissue matrices of dogs suffering from malignant canine mammary tumors in Punjab, India. Heliyon. 2020 Oct 29;6(10):e05274. doi: 10.1016/j.heliyon.2020.e05274. PMID: 33163644; PMCID: PMC7610237. 9: Jiang M, Gao H, Liu X, Wang Y, Lan J, Li Y, Zhu K, Gong P, Lv S. Detection of pesticide residues in vegetables sold in Changchun City,China. J Food Prot. 2020 Oct 27. doi: 10.4315/JFP-20-236. Epub ahead of print. PMID: 33108463. 10: White KB, Kalina J, Scheringer M, Přibylová P, Kukučka P, Kohoutek J, Prokeš R, Klánová J. Temporal Trends of Persistent Organic Pollutants across Africa after a Decade of MONET Passive Air Sampling. Environ Sci Technol. 2020 Oct 23. doi: 10.1021/acs.est.0c03575. Epub ahead of print. PMID: 33095578. 11: Steinholt M, Xu S, Ha SO, Phi DT, Odland ML, Odland JØ. Serum Concentrations of Selected Organochlorines in Pregnant Women and Associations with Pregnancy Outcomes. A Cross-Sectional Study from Two Rural Settings in Cambodia. Int J Environ Res Public Health. 2020 Oct 20;17(20):7652. doi: 10.3390/ijerph17207652. PMID: 33092193; PMCID: PMC7589876. 12: Sundhar S, Shakila RJ, Jeyasekaran G, Aanand S, Shalini R, Arisekar U, Surya T, Malini NAH, Boda S. Risk assessment of organochlorine pesticides in seaweeds along the Gulf of Mannar, Southeast India. Mar Pollut Bull. 2020 Dec;161(Pt B):111709. doi: 10.1016/j.marpolbul.2020.111709. Epub 2020 Oct 7. PMID: 33038713. 13: Madrigal JM, Sargis RM, Persky V, Turyk ME. Multiple organochlorine pesticide exposures and measures of sex steroid hormones in adult males: Cross- sectional findings from the 1999-2004 National Health and Nutrition Examination Survey. Int J Hyg Environ Health. 2021 Jan;231:113609. doi: 10.1016/j.ijheh.2020.113609. Epub 2020 Sep 28. PMID: 33002787; PMCID: PMC7736259. 14: García Ríos A, Martínez AS, Londoño ÁL, Restrepo B, Landázuri P. Determination of organochlorine and organophosphorus residues in surface waters from the coffee zone in Quindío, Colombia. J Environ Sci Health B. 2020;55(11):968-973. doi: 10.1080/03601234.2020.1802185. Epub 2020 Sep 8. PMID: 32897838. 15: Sun X, Zhan F, Yu RQ, Chen L, Wu Y. Bio-accumulation of organic contaminants in Indo-Pacific humpback dolphins: Preliminary unique features of the brain and testes. Environ Pollut. 2020 Dec;267:115511. doi: 10.1016/j.envpol.2020.115511. Epub 2020 Aug 27. PMID: 32892017. 16: Li Y, Lohmann R, Zou X, Wang C, Zhang L. Air-water exchange and distribution pattern of organochlorine pesticides in the atmosphere and surface water of the open Pacific ocean. Environ Pollut. 2020 Oct;265(Pt A):114956. doi: 10.1016/j.envpol.2020.114956. Epub 2020 Jun 10. PMID: 32806399. 17: Carvalho RRR, Rodriguez MDVR, Franco ES, Beltrame F, Pereira AL, Santos VS, Araujo W, Rocha BA, Rodrigues JL. DLLME-SFO-GC-MS procedure for the determination of 10 organochlorine pesticides in water and remediation using magnetite nanoparticles. Environ Sci Pollut Res Int. 2020 Dec;27(36):45336-45348. doi: 10.1007/s11356-020-10285-2. Epub 2020 Aug 12. PMID: 32785893. 18: R O Varca JP, A J Martins E, H C Varca G, L Romano R, T Lebre D, E O Lainetti P, V Bustillos JO. Determination of Organochlorines in Soil of a Suburban Area of São Paulo Brazil. Int J Environ Res Public Health. 2020 Aug 5;17(16):5666. doi: 10.3390/ijerph17165666. PMID: 32764488; PMCID: PMC7459836. 19: Venugopal D, Subramanian M, Rajamani J, Palaniyappan J, Samidurai J, Arumugam A. Levels and distribution pattern of organochlorine pesticide residues in eggs of 22 terrestrial birds from Tamil Nadu, India. Environ Sci Pollut Res Int. 2020 Nov;27(31):39253-39264. doi: 10.1007/s11356-020-09978-5. Epub 2020 Jul 8. PMID: 32642894. 20: Abdel Hamid ER, Sharaf NE, Ahmed HH, Ahmed A, Mossa AH. In utero exposure to organochlorine pesticide residues and their potential impact on birth outcomes and fetal gender. Environ Sci Pollut Res Int. 2020 Sep;27(27):33703-33711. doi: 10.1007/s11356-020-09411-x. Epub 2020 Jun 12. PMID: 32533481.