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275875

Sigma-Aldrich

4-Aminopyridine

≥99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H6N2
CAS Number:
504-24-5
Molecular Weight:
94.11
Beilstein:
105782
EC Number:
207-987-9
MDL number:
MFCD00006439
UNSPSC Code:
12352100
PubChem Substance ID:
24856677
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

≥99%

form

solid

bp

273 °C (lit.)

mp

155-158 °C (lit.)

solubility

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.)

SMILES string

Nc1ccncc1

InChI

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

InChI key

NUKYPUAOHBNCPY-UHFFFAOYSA-N

Gene Information

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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General description

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].

Application

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]

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

312.8 °F

Flash Point(C)

156 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3794
MKCJ2184
MKBW8059V
MKBN8495V
MKBF7199

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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
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)
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
4-Aminopyridine derivatives with antiamnesic activity
Andreani A, et al.
European Journal of Medicinal Chemistry, 35(1), 77-82 (2000)
Silvia Ghirga et al.
Journal of the Optical Society of America. A, Optics, image science, and vision, 37(4), 643-652 (2020-05-14)
It has been recently demonstrated that the exposure of naive neuronal cells to light-at the basis of optogenetic techniques and calcium imaging measurements-may alter neuronal firing. Indeed, understanding the effect of light on nongenetically modified neurons is crucial for a
View All Related Papers

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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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