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275875

Sigma-Aldrich

4-Aminopyridine

≥99%

Sinônimo(s):

4-Pyridinamine, 4-Pyridylamine, 4AP, Fampridine

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About This Item

Fórmula empírica (Notação de Hill):
C5H6N2
Número CAS:
504-24-5
Peso molecular:
94.11
Beilstein:
105782
Número CE:
207-987-9
Número MDL:
MFCD00006439
Código UNSPSC:
12352100
ID de substância PubChem:
24856677
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Ensaio

≥99%

Formulário

solid

p.e.

273 °C (lit.)

pf

155-158 °C (lit.)

solubilidade

DMF: soluble(lit.)
DMSO: soluble(lit.)
THF: soluble(lit.)
acetone: soluble(lit.)
acetonitrile: soluble(lit.)
ethanol: soluble(lit.)
isopropanol: soluble(lit.)
methanol: soluble(lit.)
water: soluble(lit.)

cadeia de caracteres SMILES

Nc1ccncc1

InChI

1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)

chave InChI

NUKYPUAOHBNCPY-UHFFFAOYSA-N

Informações sobre genes

human ... KCNA1(3736) , KCNA10(3744) , KCNA2(3737) , KCNA3(3738) , KCNA4(3739) , KCNA5(3741) , KCNA6(3742) , KCNA7(3743) , KCNB1(3745) , KCNB2(9312) , KCNC1(3746) , KCNC2(3747) , KCNC3(3748) , KCNC4(3749) , KCND1(3750) , KCND2(3751) , KCND3(3752) , KCNF1(3754) , KCNG1(3755) , KCNG2(26251) , KCNG3(170850) , KCNG4(93107) , KCNH1(3756) , KCNH2(3757) , KCNH3(23416) , KCNH4(23415) , KCNH5(27133) , KCNH6(81033) , KCNH7(90134) , KCNH8(131096) , KCNQ1(3784) , KCNQ2(3785) , KCNQ3(3786) , KCNQ4(9132) , KCNQ5(56479) , KCNS1(3787) , KCNS2(3788) , KCNS3(3790) , KCNV1(27012) , KCNV2(169522)
mouse ... Kcna3(16491)
rat ... Grin2a(24409)

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Descrição geral

4-Aminopyridine (4-AP) blocks the voltage-dependent potassium channels in other nerve membranes[1]. 4-AP is a K+ channel blocker and causes epileptiform activity in in vitro preparations and is a potent convulsant in animals and man[2].

Aplicação

4-Aminopyridine can be used as:
  • A reactant to prepare pharmacologically important 4-amino-N-pyridin-4-yl-butyramide hydrochloride.[3]
  • A reactant to prepare cinnamic acid derivatives as potent cholinesterase inhibitors.[4]
  • A starting material to prepare aza analogs of batracylin, a topoisomerase II inhibitor.[5]

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Chronic 2 - Eye Dam. 1 - Skin Corr. 1B

Código de classe de armazenamento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

312.8 °F

Ponto de fulgor (°C)

156 °C

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificados de análise (COA)

Lot/Batch Number
MKCQ3794
MKCJ2184
MKBW8059V
MKBN8495V
MKBF7199

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H Bostock et al.
The Journal of physiology, 313, 301-315 (1981-01-01)
1. 4-Aminopyridine (4AP) and tetraethylammonium ions (TEA), which block voltage-dependent potassium channels in other nerve membranes, have been used to study nerve conduction in fibres of normal rat spinal roots and those demyelinated with diphtheria toxin. The pharmacological actions have
Synthesis of aza analogues of the anticancer agent batracylin
Martinez-Viturro CM and Dominguez D
Tetrahedron Letters, 48(27), 4707-4710 (2007)
Design, synthesis and evaluation of novel cinnamic acid derivatives bearing N-benzyl pyridinium moiety as multifunctional cholinesterase inhibitors for Alzheimer′s disease
Lan J-S, et al.
Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 776-788 (2017)
S Yamaguchi et al.
Epilepsy research, 11(1), 9-16 (1992-03-01)
The K+ channel blocker 4-aminopyridine (4-AP) causes epileptiform activity in in vitro preparations and is a potent convulsant in animals and man. In mice, 4-AP produces behavioral activation, clonic limb movements and wild running, followed by tonic hindlimb extension and
Maxime Lévesque et al.
Epilepsia, 54(4), 596-604 (2013-03-26)
The K(+) channel blocker 4-aminopyridine (4AP) induces epileptiform synchronization in brain slices maintained in vitro without interfering with γ-aminobutyric acid (GABA)A receptor-mediated inhibition and, actually, even enhancing it. The hypothesis that similar electrographic epileptiform patterns occur in vivo following systemic
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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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