| Identification | More | [Name]
4-Aminopyridine | [CAS]
504-24-5 | [Synonyms]
4-AP
4APY
4-pyridinamine
4-PYRIDYLAMINE
AKOS 91150
Amino-4-pyridine
AMINOPYRIDINE, 4-
AURORA KA-676
avitrol
AVITROL(R)
FAMPRIDINE
GAMMA-AMINOPYRIDINE
GAMMA-PYRIDYLAMINE
P-AMINO PYRIDINE
PYRIDIN-4-AMINE
PYRIDIN-4-YLAMINE
γ-Pyridylamine
TIMTEC-BB SBB004393
4-amino-pyridin
Avitrol 200 | [EINECS(EC#)]
207-987-9 | [Molecular Formula]
C5H6N2 | [MDL Number]
MFCD00006439 | [Molecular Weight]
94.11 | [MOL File]
504-24-5.mol |
| Chemical Properties | Back Directory | [Appearance]
4-Aminopyridine is white to tan or brown crystalline material. Odorless. | [Melting point ]
155-158 °C (lit.) | [Boiling point ]
273 °C (lit.) | [density ]
1.26 | [vapor pressure ]
0.046Pa at 25℃ | [refractive index ]
1.5560 (estimate) | [Fp ]
156°C | [storage temp. ]
0-6°C | [solubility ]
H2O: soluble50mg/mL, clear, colorless | [form ]
Crystalline Powder, Solid or Crystals | [pka]
9.114(at 25℃) | [color ]
White to faint grey to light yellow | [Water Solubility ]
Soluble in water(112 g/L at 20 deg C). Soluble in ethyl ether, benzene. Slightly soluble in ligroin. Very soluble in ethanol. Soluble in methanol, acetone, tetrahydrofuran, isopropanol, acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, and ethanol. | [Merck ]
14,3933 | [BRN ]
105782 | [Stability:]
Hygroscopic | [InChIKey]
NUKYPUAOHBNCPY-UHFFFAOYSA-N | [LogP]
-0.76 at pH7.4 | [CAS DataBase Reference]
504-24-5(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Pyridinamine(504-24-5) | [EPA Substance Registry System]
504-24-5(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
4-aminopyridine(504-24-5) is a white crystalline solid that contains about 98% active ingredient. It is soluble in water and slightly soluble in benzene and ether. 4-Aminopyridine formulations are classifi ed by the US Environmental Protection Agency (US EPA) as restricted
use pesticides (RUPs) and therefore should be purchased and used only by certifi ed and
trained workers and applicators. Avitrol is available as grain baits or as a powder concentrate. It is one of the most prominent avicides. It is registered with the EPA for use against
red-winged blackbirds, blackbirds in agricultural fi elds, grackles, pigeons, and sparrows
around public buildings, and various birds around livestock feeding pens. Avitrol repels
birds by poisoning a few members of a fl ock, causing them to become hyperactive.
| [General Description]
White crystalline material with no odor. Used as an avicide, an intermediate and as a fixer for some textile dyes. | [Reactivity Profile]
PYRIDINE, 4-AMINO-neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. | [Health Hazard]
4-Aminopyridine, a pyridine compound, is an extremely effective bird poison. In agriculture, 4-AP is used as an extremely effective bird poison sold under the brand name Avitrol.
It is highly toxic to all mammals including humans if dosages are exceeded, and as an
experimental drug, the recommended dose data is unavailable. 4-Aminopyridine blocks | [Health Hazard]
Material may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Material affects neural transmission. In sufficient concentrations, material may cause metabolic acidosis, respiratory arrest, and cardiac arrhythmias. | [Potential Exposure]
Used as a chemical intermediate in pharmaceuticals; as an agricultural chemical for field crops; and as a bird repellent and poison | [Fire Hazard]
Material may produce irritating or poisonous gases in fire. Runoff from fire control water may give off irritating or poisonous gases. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. | [Shipping]
UN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials | [Incompatibilities]
Sodium nitrite, strong oxidizers. Avoid contact with acid anhydrides, acid chlorides; and strong acids. | [Description]
4-Aminopyridine (4-AP, fampridine, dalfampridine,504-24-5) is the first drug approved by the FDA to improve walking in patients with multiple sclerosis (MS). Dalfampridine is a voltage-gated potassium channel blocker that readily penetrates the CNS and increases the conduction and duration of action potential across nerve fibers resulting in enhanced functionality as observed in the walking speed of MS patients.
From a safety perspective, seizure was the most important adverse event from various dalfampridine clinical trials. Therefore, dalfampridine is contraindicated in patients with a history of seizures. Since dalfampridine is primarily excreted by the kidney as unchanged drug, it is also contraindicated in patients with moderate to severe renal impairment. Assessing the overall benefit–risk profile from various clinical trials, the FDA approved dalfampridine (daily oral dose of 10 mg, b.i.d.) to improve walking in MS patients with existing gait impairment.
| [Waste Disposal]
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposalIncineration with nitrogen oxides removal from effluent gas. | [Originator]
Rush University Medical Center (United States) | [Uses]
Avitrol (4-aminopyridine), has repellent–toxicant properties for birds and is classed as a severe poison and irritant. This secondary bird repellent can be used as a broadcast bait, causing uncoordinated flight and distress calls and escape responses in nearby birds. | [Uses]
Dalfampridine is used in characterizing subtypes of potassium channel, and has also been used to manage some of the symptoms of multiple sclerosis, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. Dalfampridine is a precursor to the drug Pinacidil. | [Uses]
vasodilator | [Definition]
ChEBI: An aromatic amine that is pyridine bearing a single amino substituent at position 4. An orphan drug in the US, it is used to improve walking in adults with multiple sclerosis. | [Brand name]
Neurelan (E′lan);Ampyra. | [Synthesis Reference(s)]
Tetrahedron Letters, 39, p. 1313, 1998 DOI: 10.1016/S0040-4039(97)10877-2 | [in vitro]
4-ap acts by selectively blocking fast, voltage-gated k+ channels in excitable tissues. in axons, k+ channel blockade increases the safety factor1 across demyelinated internodes and 4-ap can, therefore, restore conduction in focally demyelinated axons. 4-ap also increases calcium (ca2+) influx at presynaptic terminals thereby enabling an enhancement of neuroneuronal or neuromuscular transmission in normally myelinated neurons [1]. | [in vivo]
investigations of the effects of 4-ap on neurologic deficits in animal in vivo models of demyelinating disease or sci have yielded inconsistent results. some trials have shown indications of potential neurological benefit, such as enhanced motor evoked potentials or reflex activity, while others have yielded no evident gains in function [1]. | [IC 50]
170 and 230 μm at kv1.1 and kv1.2, respectively | [Environmental Fate]
4-AP produces toxicity through multiple mechanisms. At toxic
doses, 4-AP blocks voltage-sensitive K+ ion channels and
increases acetylcholine levels at the synapses and neuromuscular
junctions. This results in hyperactivity, convulsions, and seizures. 4-AP also causes excess methemoglobin formation,and methemoglobin is unable to carry oxygen to the tissues,
thereby causing respiratory distress. Death occurs due to cardiac
and respiratory arrest. Because 4-AP blocks voltage-sensitive K+
channels in neurons, it has the capacity to enhance action
potential conduction in demyelinated tissue with therapeutically
beneficial results. | [storage]
Room temperature | [Purification Methods]
Crystallise the aminopyridine from *benzene/EtOH, then recrystallise it twice from water, then crush and dry it for 4hours at 105o [Bates & Hetzer J Res Nat Bur Stand 64A 427 1960]. It has also been crystallised from EtOH, *benzene, *benzene/pet ether, toluene and sublimes in a vacuum. [Beilstein 22/9 V 106.] | [Toxicity evaluation]
4-AP(504-24-5) is adsorbed to soil particles and is moderately persistent
in the environment. It has been reported to be slowly metabolized
by soil microorganisms. The rate of disappearance varies
with the organic content of soils, and the disappearance halftime
has been reported to range from 3 to 32 months. Movement
from upper soil layers is thought to be minimal due to
strong soil adsorption, and the compound is not expected to
represent a significant threat to groundwater.
| [References]
[1] hayes kc. the use of 4-aminopyridine (fampridine) in demyelinating disorders. cns drug rev. 2004 winter;10(4):295-316. |
| Safety Data | Back Directory | [Hazard Codes ]
T+,N,T,Xi | [Risk Statements ]
R28:Very Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S37/39:Wear suitable gloves and eye/face protection .
S1:Keep locked up . | [RIDADR ]
UN 2671 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
US1750000
| [F ]
8-21 | [Autoignition Temperature]
640 °C | [Hazard Note ]
Toxic/Irritant | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29333999 | [Safety Profile]
Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: hallucinations and vomiting. When heated to decomposition it emits toxic fumes of NOx,. | [Hazardous Substances Data]
504-24-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 21 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Potassium carbonate-->Phthalic acid-->Pyridine-N-oxide-->4-Nitropyridine | [Preparation Products]
4-ACETAMIDO-3-AMINOPYRIDINE-->(3-BROMO-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER-->2,2-DIMETHYL-N-PYRIDIN-4-YL-PROPIONAMIDE-->4-(Boc-amino)pyridine-->3-PYRIDINEACETIC ACID, 4-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-A-OXO-, ETHYL ESTER-->TERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE-->efficient polymer catalyst for acrylation-synthesis and characterigation of polyamide containing supernucleophilic reagent-->4-Iodopyridine-->2-chloro-5-ethylaminomethylpyridine-->4-Amino-3-nitropyridine-->4-Amino-2-bromopyridine-->4-PYRIDYLTHIOUREA-->3,4-DiaMino-5-broMo-2-chloropyridine-->4-chloropyridine-->2,7-di(pyridin-4-yl)benzo[lMn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone-->4-Amino-3-(trifluoromethyl)pyridine |
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