IDPN (chemical)

IDPN

Names
Preferred IUPAC name

3,3′-Azanediyldipropanenitrile

Other names

Bis(2-cyanoethyl)amine

Identifiers

CAS Number

* 111-94-4

3D model (JSmol)

* Interactive image

ChemSpider |

* 7857

EC Number |

* 203-922-3

PubChem CID

* 8149

UNII |

* 3XP1CVU865

UN number | 3334

InChI

* InChI=1S/C6H9N3/c7-3-1-5-9-6-2-4-8/h9H,1-2,5-6H2

Key: SBAJRGRUGUQKAF-UHFFFAOYSA-N

SMILES

* C(CNCCC#N)C#N

Properties

Chemical formula

| C6H9N3
Molar mass | 123.159 g·mol−1
Density | 1.02
Melting point |  −5.5 °C (22.1 °F; 267.6 K)
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H319, H335

GHS precautionary statements

| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

IDPN (3,3'-iminodipropanenitrile) is a neurotoxin with ototoxic and hepatotoxic effects. It causes irreversible movement disorder.[1][2][3]

## Ototoxicity

IDPN has been shown to kill vestibular hair cells, disrupting normal vestibular function, in rats,[4] mice, guinea pigs, and frogs.[5] In rodents, the loss of vestibular function results in balance-related deficits, including circling behavior, retropulsion, and head bobbing, as well as weight loss.[5] Type I hair cells are more sensitive to IDPN toxicity than Type II hair cells.[4] No regeneration of vestibular hair cells was observed, thus these effects can be considered to be irreversible.[4]

IDPN has also been shown to kill cochlear hair cells, affecting auditory function.[6] IDPN-induced hearing loss covered a broad range of frequencies.

## References

1. ↑ Sedó-Cabezón, Lara; Jedynak, Paulina; Boadas-Vaello, Pere; Llorens, Jordi (1 October 2015). "Transient alteration of the vestibular calyceal junction and synapse in response to chronic ototoxic insult in rats". Disease Models & Mechanisms 8 (10): 1323–1337. doi:10.1242/dmm.021436. PMID 26398945.
2. ↑ Khan, HA; Ibrahim, KE (12 October 2015). "Pattern of neurobehavioral and organ-specific toxicities of β, β'-iminodipropionitrile in mice". Archives of Medical Science 11 (5): 1137–44. doi:10.5114/aoms.2015.54871. PMID 26528360.
3. ↑ Ogata, Keiko; Kushida, Masahiko; Miyata, Kaori; Sumida, Kayo; Takeda, Shuji; Izawa, Takeshi; Kuwamura, Mitsuru; Yamate, Jyoji (2016). "Alteration of microRNA expressions in the pons and medulla in rats after 3,3′-iminodipropionitrile administration". Journal of Toxicologic Pathology 29 (4): 229–236. doi:10.1293/tox.2016-0019. PMID 27821907.
4. ↑ 4.0 4.1 4.2 Llorens, J.; Demêmes, D. (1994-06-01). "Hair cell degeneration resulting from 3,3'-iminodipropionitrile toxicity in the rat vestibular epithelia". Hearing Research 76 (1–2): 78–86. doi:10.1016/0378-5955(94)90090-6. ISSN 0378-5955. PMID 7928719.
5. ↑ 5.0 5.1 Soler-Martín, Carla; Díez-Padrisa, Núria; Boadas-Vaello, Pere; Llorens, Jordi (2007-03-01). "Behavioral Disturbances and Hair Cell Loss in the Inner Ear Following Nitrile Exposure in Mice, Guinea Pigs, and Frogs" (in en). Toxicological Sciences 96 (1): 123–132. doi:10.1093/toxsci/kfl186. ISSN 1096-6080. PMID 17159233.
6. ↑ Crofton, K. M.; Janssen, R.; Prazma, J.; Pulver, S.; Barone, S. (November 1994). "The ototoxicity of 3,3'-iminodipropionitrile: functional and morphological evidence of cochlear damage". Hearing Research 80 (2): 129–140. doi:10.1016/0378-5955(94)90104-X. ISSN 0378-5955. PMID 7896571.

* v
* t
* e

Neurotoxins

Animal|

* Batrachotoxin
* Bestoxin
* Birtoxin
* Bungarotoxin
* Charybdotoxin
* Conotoxin
* Fasciculin
* Huwentoxin
* Poneratoxin
* Saxitoxin
* Tetrodotoxin
* Vanillotoxin
* Spooky toxin (SsTx)
* Epibatidine
* Zetekitoxin AB
* Dendrotoxin

Bacterial|

* Botulinum toxin
* Tetanospasmin

Cyanotoxins|

* Anatoxin-a
* Anatoxin-a(S)
* BMAA
* Saxitoxin

Plant|

* Bicuculline
* Penitrem A
* Picrotoxin
* Strychnine
* Tutin
* Rotenone
* Ginkgotoxin
* Cicutoxin
* Oenanthotoxin
* Thujone
* Volkensin

Mycotoxins|

* Ibotenic acid
* Muscarine
* Muscimol

Pesticides|

* Fenpropathrin
* Tetramethylenedisulfotetramine
* Bromethalin
* Crimidine
* Methamidophos
* Endosulfan
* Fipronil
* Phenylsilatrane
* Chlorophenylsilatrane
* Sulfuryl fluoride
* Mipafox
* Schradan
* Dimefox

Nerve agents|

* Cyclosarin
* EA-3148
* Novichok agent
* Sarin
* Soman
* Tabun
* VE
* VG
* VM
* VP
* VR
* VX
* GV
* EA-3990
* EA-4056
* T-1123
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* Fluorotabun
* Chinese VX
* EA-2192

Bicyclic phosphates|

* TBPS
* TBPO
* IPTBO

Other|

* Dimethylmercury
* Toxopyrimidine
* IDPN

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:IDPN_(chemical)&oldid=768666"
*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
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