Furfuryl(purin-6-yl)amin

Kinetin

HCID 3830CAS 525-79-1

Grundinformationen

Standard-SMILES
c1coc(CNc2ncnc3nc[nH]c23)c1
InChIKey
QANMHLXAZMSUEX-UHFFFAOYSA-N
Summenformel
C10H9N5O
Durchschnittliche Molmasse
215,21 g/mol
Monoisotopische Masse
215,08070991

Überblick

Kinetin is a member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group. It has a role as a geroprotector and a cytokinin. It is a member of 6-aminopurines and a member of furans.

Namen und Bezeichner

Bevorzugter Name
Kinetin
IUPAC
N-(furan-2-ylmethyl)-7H-purin-6-amine
Lokaler Name
Furfuryl(purin-6-yl)amin
Englischer Name
Kinetin
Summenformel
C10H9N5O
Molmasse
215.21

Namen und Synonyme

kinetin525-79-16-Furfurylaminopurine6-Furfuryladenine6-(Furfurylamino)purineN6-FurfuryladenineN-FurfuryladenineCytokininN-(furan-2-ylmethyl)-7H-purin-6-amineAdenine, N-furfuryl-Furfuryl(purin-6-yl)amine1H-PURIN-6-AMINE, N-(2-FURANYLMETHYL)-
Weitere Namen anzeigen
KTfapKINETINEN-(2-Furylmethyl)-9H-purin-6-amineKinetinaN-[(Fur-2-yl)methyl]-9H-purin-6-amine
N(sup 6)-FurfuryladenineN-(2-Furanylmethyl)-1H-purin-6-amineDTXSID9035175NSC-23119P39Y9652YJDTXCID7015175CHEBI:274076 furfurylaminopurine

Datenbank-Bezeichner

CAS
525-79-1
PubChem CID
3830
DTXSID
DTXSID9035175
ChEMBL
CHEMBL228792
ChEBI
CHEBI:27407
UNII
P39Y9652YJ
EC Number
208-382-2
Nikkaji
J6.656G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1
Polarare Oberfläche (TPSA)
79,6 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
3
Schwere Atome
16

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning
PesticidesPesticides -> Plant Growth Regulators
Color/FormPlatelets from absolute ethanol
SolubilitySlightly soluble in cold water, methanol, ethanol. Freely soluble in dilute aqueous hydrochloric acid or sodium hydroxide.
DecompositionWhen heated to decomposition it emtis toxic vapors of /nitrogen oxides/.

Physikochemische Eigenschaften

Schmelzpunkt
269 · 269-271 °C (dec.)(lit.)
Siedepunkt
355.49 °C · 355.49°C (rough estimate)
Dichte
1.2639 · 1.2639 (rough estimate)
Brechungsindex
1.761 · 1.7610 (estimate)
Flammpunkt
269 · 269-271°C
storage temp.
-70 °C · -70°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 9.7% (9 of 93) of reports.

Warning

H341 (87.1%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 93 reports by companies from 7 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information1H-Purin-6-amine, N-(2-furanylmethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1H-Purin-6-amine, N-(2-furanylmethyl)-: Environment tier I assessment
Hazards SummaryAn irritant; [MSDSonline]
Special Reports · 1 Eintrag

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Cytokinin. EPA 078-R-95-025 December 1995. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 6, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]

FIFRA Requirements · 3 Einträge

An exemption from the requirement of a tolerance is established for residues of cytokinins (specifically: aqueous extract of seaweed meal and kinetin) in or on all food commodities when used as plant regulators on plants, seeds, or cuttings and on all food commodities after harvest in accordance with good agricultural practices.

Based on the reviews of the generic data for the active ingredients Cytokinin, the Agency has sufficient information on the health effects of Cytokinin and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that Cytokinin products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing Cytokinin for registered uses listed below are eligible for product reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Kinetin is found on List D. Case No: 4107; Pesticide type: herbicide; Case Status: RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): kinetin; Data Call-in (DCI) Date(s): 09/21/93; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Hazard Classes and CategoriesMuta. 2 (87.1%)

Sicherheit und Schutzausrüstung

Storage Conditions · 2 Einträge

Store in a cool place out of direct sunlight. Temperatures <32 °F or >105 °F may cause product deterioration.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

Cleanup Methods · 2 Einträge

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

Disposal Methods · 3 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Preventive Measures · 4 Einträge

Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.

Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.

Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.

Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

Allowable Tolerances · 1 Eintrag

An exemption from the requirement of a tolerance is established for residues of cytokinins (specifically: aqueous extract of seaweed meal and kinetin) in or on all food commodities when used as plant regulators on plants, seeds, or cuttings and on all food commodities after harvest in accordance with good agricultural practices.

Toxikologische Informationen

Interactions · 1 Eintrag

The effects of a long-term (15 day) or short-term (3 or 15 h) treatment with 1 mM aluminium on peroxidase activity, lipid peroxidation and multiplication rate (15 day) were evaluated in Lemna minor L. Kinetin or citrate were administered together with Al in the culture medium in the long-term study or immediately after Al treatment in the short-term study, to mitigate Al toxicity. ... Increments in enzyme activity and lipid peroxidation and a decrease in multiplication rate were observed after Al treatments. Citrate was capable of lowering the Al-induced increase in peroxidase activity in the long- and short-term treatments. The large increase in lipid peroxidation induced by Al was blocked by kinetin and, to a lesser extent, by citrate; the latter more effectively limited the decrease in multiplication rate induced by Al.

Ecotoxicity Values · 4 Einträge

LD50 Colinus virginianus (Bobwhite quail, 21 weeks old) oral >2510 mg/kg

EC50 Daphnia magna (Water flea; intoxication, immobilization) >1000 ppm/48 hr; static /formulated product/

LC50 Oncorhynchus mykiss (Rainbow trout) >1000 ppm/96 hr; static /formulated product/

LC50 Lepomis macrochirus (Bluegill) >1000 ppm/96 hr; static /formulated product/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 612(SRC), determined from a structure estimation method(2), indicates that kinetin is expected to have low mobility in soil(SRC). Volatilization of kinetin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Kinetin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2006).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 612(SRC), determined from a structure estimation method(2), indicates that kinetin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.60(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), kinetin, which has an estimated vapor pressure of 1.8X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase kinetin may be removed from the air by wet and dry deposition(SRC).

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for kinetin can be estimated to be 612(SRC). According to a classification scheme(2), this estimated Koc value suggests that kinetin is expected to have low mobility in soil(SRC).

Human Toxicity Excerpts · 2 Einträge

/OTHER TOXICITY INFORMATION/ ... The amount of kinetin in urine taken from unhealthy patient's lung carcinoma was established to be 0.5 ng in 20 ml and a 100-fold reduced amount in healthy subjects.

/OTHER TOXICITY INFORMATION/ ... An addition of 40 to 200 microM kinetin (Kn) in the culture medium of human diploid fibroblasts can both delay the onset and decrease the extent of many of the ageing characteristics that appear during serial passaging of normal cells in culture.

Artificial Pollution Sources · 1 Eintrag

Kinetin's production may result in its release to the environment through various waste streams; it's use as a plant growth regulator(1) will result in its direct release to the environment(SRC). Kinetin is also used in cosmetic products to reduce the appearance of wrinkles, hyperpigmentation and roughness of the skin(2).

Regulatorische Informationen

FIFRA Requirements · 3 Einträge

An exemption from the requirement of a tolerance is established for residues of cytokinins (specifically: aqueous extract of seaweed meal and kinetin) in or on all food commodities when used as plant regulators on plants, seeds, or cuttings and on all food commodities after harvest in accordance with good agricultural practices.

Based on the reviews of the generic data for the active ingredients Cytokinin, the Agency has sufficient information on the health effects of Cytokinin and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that Cytokinin products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing Cytokinin for registered uses listed below are eligible for product reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Kinetin is found on List D. Case No: 4107; Pesticide type: herbicide; Case Status: RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): kinetin; Data Call-in (DCI) Date(s): 09/21/93; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29349990
RTECS-Nr.
AU6270000
risk_code
68-36/37/38
Toxizität
LD50 intraperitoneal in mouse: 450mg/kg

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.

Verwendung und Herstellung

Uses · 6 Einträge

A cell division factor present in plants and yeast; [Merck Index] Used to stimulate plant growth, to augment growth of microbial cultures, and in cosmetics to reduce wrinkles, hyperpigmentation, and roughness; [HSDB] Promotes leaf expansion and retards leaf aging; Applied to growing crops (vegetables and fruits); Cytokinin is naturally occurring and derived from seaweed meal; Kinetin is synthetic cytokinin; [Reference #1]

Farming (Pesticides) [Category: Industry]

For kinetin (USEPA/OPP Pesticide Code: 116802) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Plant growth regulator. To augment growth of microbial cultures.

Plant growth regulator, biostimulant. For alfalfa, corn, cotton, peanuts, rice, sorghum, soybeans, sugar beets, triticale, wheat, fruits, and vegetables to increase yields; to ornamentals, trees and turf to increase growth and development.

A plant growth regulator used to promote growth in bacteria cultures and as a dormancy breaker.

Methods of ManufacturingStructure and synthesis from furfurylamine and 6-methylmercaptopurine: Miller et al. J Am Chem Soc 78: 1375 (1956); US 2903455
Formulations/Preparations · 5 Einträge

Liquid concentrate

Other products mixtures: Cytoplex HMS (+4-indol-3-ylbutyric acid + gibberellic acid), Green Sol 48 (+ gibberellic acid).

Trade names: X-Cyte; X-Cyto

Trade names: Cytex, Nitrozyme, Cytogen, and Burst Yield Booster

Manufacturing products: Form not identified/liquid- 0.01 to 0.01%; Soluble concentrate/liquid- 0.0040 to 0.0120%. End use products: Flowable concentrate- 0.004 to 0.0096%; Liquid-ready to use- 0.00008 to 0.00008%; Soluble concentrate/liquid- 0.0003 to 0.0400%.

Use ClassificationCosmetics -> Skin conditioning
General Manufacturing Information · 2 Einträge

9H-Purin-6-amine, N-(2-furanylmethyl)-: ACTIVE

Cytokinins are a group of naturally occurring plant growth regulators, all derivatives of adenine. They are often extracted commercially from seaweeds, but occur in most other plants. Important natural cytokinins include: kinetin, called 'synthetic cytokinin' because, although naturally occurring, it is not found in plants; zeatin, first isolated from corn (Zea mays); and 6-isopentenylaminopurine, isolated from tissue cultures of tobacco. Many synthetic cytokinins, e.g. 6-benzylaminopurine (q.v.) are now known. /Cytokinins/

Anwendungen · 2 Einträge

BeschreibungKinetin (or Vivakin) was introduced as Kinerase in the US as a new ingredient for the treatment of age related photodamage of skin. This 6- furfurylaminopurine is a synthetic cytokinin, a family of plant growth factors, and was shown to be a highly potent growth factor. In vitro, it was able to delay or prevent the onset of age-related changes in skin cells without affecting cellular lifespan. In a double-blind clinical trial, Kinetin (0.005%) partially reversed the clinical signs of photodamaged skin and demonstrated a good safety profile. It could have potential in psoriasis as well as in other proliferative skin disorders.

VerwendenKinetin acts as plant growth accelerator, auxin, plant growth regulator, plant cell division promotor. It also acts as cell division factor found in various plant parts and in yeast. A plant growth regulator. Augments growth of microbial cultures.

Anbieter50 Anbieter

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